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Research Article  |  Open Access  |  23 Mar 2023

Acyl transfer-enabled catalytic asymmetric Michael addition of α-hydroxy-1-indanones to nitroolefins

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Chem Synth 2023;3:17.
10.20517/cs.2022.35 |  © The Author(s) 2023.
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Abstract

We report herein an enantioselective acyl transfer protocol via electrophile activation. The reaction cascade sequence encompasses dinuclear zinc-catalyzed asymmetric Michael addition, intramolecular cyclization, and retro-Claisen reaction, which leads to a step- and atom-economic approach to a variety of protected cyclic tertiary α-hydroxyketones in good yields with excellent enantioselectivities (24 examples, 56%-82% yield, 1.5-13 dr and 79%-96% ee). Besides, the large-scale synthesis and further transformation of the products demonstrate the effectiveness of this method for organic synthesis.

Keywords

Acyl transfer, retro-Claisen reaction, zinc catalyst, nitroolefins, α-hydroxy-1-indanones

INTRODUCTION

Acyl transfer presents an omnipresent and efficient chemoselective ligation process in biological systems[1], which has attracted extensive attention in the chemical community in recent years[2]. In order to circumvent intrinsic reactivity or selectivity issues associated with mono-activated reactants, acyl transfer strategy utilizes the acyl group as a transient activating group to produce bis-activated reactants [Scheme 1A]. Such a chemical event involves a reaction cascade of X-Y bond formation, intramolecular cyclization, and the retro-Claisen reaction, where the challenging mono-activated function could be implemented formally. In this context, several catalytic asymmetric acyl transfer methods have been developed based on nucleophile activation [Scheme 1B]. For example, Mondal, Song et al. developed the asymmetric cascade Michael/acyl transfer reactions of α-nitroketones and 1,3-diketones using bifunctional organocatalysts[3-11]. Rodriguez and Luo reported the secondary or primary amine-catalyzed acyl transfer reactions[12-16]. Very recently, Yi et al. have established an elegant iridium-catalyzed asymmetric cascade allylation/acyl transfer reaction for the synthesis of enantiomerically enriched 3-hydroxymethyl pentenal units[17]. Besides, using acyl transfer, Zhou, Yang et al. prepared the medium-sized-ring lactams from cyclobutanone β-ketoamides[18-21]. Despite these achievements via nucleophile activation, acyl transfer via electrophile activation remains far less developed [Scheme 1C]. As far as we know, there was only one example from the Pan group, where nitroenone was used as an electrophilic acyl transfer reagent in catalytic asymmetric Friedel-Crafts and Michael reactions[22]. Therefore, the development of new catalytic asymmetric acyl transfer methods via electrophile activation is highly desired.

Acyl transfer-enabled catalytic asymmetric Michael addition of <i>α</i>-hydroxy-1-indanones to nitroolefins

Scheme 1. Acyl transfer strategies in asymmetric synthesis.

Our group has a long-standing interest in developing facile protocols for synthesizing biologically important molecules. Recently, we have discovered that α-hydroxy-1-indanones could serve as a valid synthon in cyclization reactions with activated Michael acceptors via chiral dinuclear zinc catalysis[23,24]. Along this line, we envisioned that dinuclear zinc-catalyzed asymmetric acyl transfer reaction between α-hydroxy-1-indanones 1 and nitroenones 2 was feasible via less-explored electrophile activation mechanism, generating thereby the protected cyclic tertiary α-hydroxyketones 3 in an enantioselective, step- and atom-economic manner. As illustrated in Scheme 2, the reaction cascade was triggered by dinuclear zinc-catalyzed Michael reaction[25,26], which led to the intermediate Int-1. The subsequent intramolecular cyclization/retro-Claisen reaction resulted in the acyl transfer product 3. However, therein lie several synthetic organic chemistry challenges to this reaction proposal, which include: the enantioselective formation of the tetrasubstituted stereocenter, the side-formations of potential interruption product hemiketal Int-2 and dehydration product dihydrofuran 4. Herein, we introduce a highly enantioselective acyl transfer protocol via under-exploited electrophile activation by making use of dinuclear zinc-catalyzed Michael/cyclization/retro-Claisen reaction cascade, which led to a step- and atom-economic access to a variety of protected cyclic tertiary α-hydroxyketones in good yields with excellent enantioselectivities.

Acyl transfer-enabled catalytic asymmetric Michael addition of <i>α</i>-hydroxy-1-indanones to nitroolefins

Scheme 2. Our designed catalytic asymmetric acyl transfer methods via electrophile activation.

EXPERIMENTAL

Under a nitrogen atmosphere, a solution of diethylzinc (20 μL, 1.0 M in hexane, 0.02 mmol) was added dropwise to a solution of L4 (0.01 mmol, 9.6 mg) in MeCN (2 mL). After the mixture was stirred for 30 min at 30 oC, 1a (0.2 mmol, 29.6 mg) and 2a (0.2 mmol, 50.6 mg) were added. The reaction mixture was stirred for 48 h at the same temperature. The reaction was quenched with HCl solution (1 M, 2 mL), and the organic layer was extracted with CH2Cl2 (3 × 5 mL). The combined organic layer was washed with brine and dried over Na2SO4. The solvent was removed under reduced pressure by using a rotary evaporator. The residue was purified by flash chromatography with petroleum ether/ethyl acetate (4:1) to afford the desired chiral product 3a.

RESULTS AND DISCUSSION

The model reaction between α-hydroxy-1-indanone 1a and 2-nitro-1,3-diphenylprop-2-en-1-one 2a was initially performed in the presence of 10 mol % of dinuclear zinc catalyst in situ generated from 10 mol % of ligand L1 and 20 mol % of ZnEt2 in tetrahydrofuran (THF) at 30 oC oC Figure 1. The desired product 3a was obtained in 56% yield with 1.5:1 diastereoselectivity and 39% ee value [Table 1, entry 1]. The screening of different chiral ligands including ProPhenol ligands (L2-L5) and AzePhenol ligands (L6-L8) indicated that L4 bearing 4-CF3C6H4 groups was the best ligand [Table 1, entries 2-8]. Subsequently, the examination of solvent effect demonstrated that MeCN could give a high ee value of 84% [Table 1, entries 9-13]. Unfortunately, raising or lowering the reaction temperature failed to optimize the efficiency and stereoselectivity. [Table 1, entries 14-17]. Finally, we turned our attention to investigating the catalyst loading, and found that by utilizing 5 mol % of ligand L1 and 10 mol % of ZnEt2, the yield and stereoselectivity could be improved to a high level (82% yield, 88% ee, 3:1 dr) [Table 1, entries 18-20].

Acyl transfer-enabled catalytic asymmetric Michael addition of <i>α</i>-hydroxy-1-indanones to nitroolefins

Figure 1. Reaction condition screening.

Table 1

Condition ptimizationa

EntryLsolventxT (oC)yieldb (%)drceed (%)
1L1THF1030561.5:139
2L2THF1030543.5:135
3L3THF1030613.3:169
4L4THF1030653.5:177
5L5THF1030553.1:137
6L6THF1030451.1:137
7L7THF1030391.2:123
8L8THF1030491:137
9L4PhMe1030562.8:160
10L4MeCN1030713:184
11L4CH2Cl21030652.7:175
12L4CHCl31030701.7:159
13L4PhCF31030602.1:163
14L4MeCN100461.5:140
15L4MeCN1010693:180
16L4MeCN1040713:184
17L4MeCN1050693:182
18L4MeCN330543:185
19L4MeCN530823:188
20L4MeCN1530743:180

With the best conditions in hand, the scope of both nitroenones and α-hydroxy-1-indanones for the projected reaction was examined [Scheme 3]. Firstly, the Ar1 group of nitroenones was studied. A range of ortho-, meta-, para-substituted phenyl substrates 2 had been successfully employed to afford the corresponding products 3b-3f in 56%-74% yields, 1.5:1-8.3:1 diastereoselectivities and 82%-94% enantioselectivities. In addition, 1-naphthyl group was also well tolerated, giving the desired product 3g in 54% yield, 4.5:1 dr and 82% ee value. Next, the scope of Ar2 group appended to the double bond of nitroenones was investigated. As illustrated in Scheme 3, both electron-rich and electron-deficient aryl groups could be tolerated, delivering the corresponding products 3h-3k in 54%-79% yields, 2.8:1-9:1 diastereoselectivities and 79%-91% enantioselectivities. Furthermore, incorporating a heteroaromatic group (Ar2 = 2-furyl) or a sterically bulky group (Ar2 = 1-naphthyl) did not affect the efficiency of the reaction (3l and 3m). Currently, only nitroenones bearing different aromatic substituents have been examined. Subsequently, we investigated the substrate generality of α-hydroxy-1-indanones by reacting them with 1-(2-methoxyphenyl)-2-nitro-3-phenylprop-2-en-1-one 2f. Different substituents (from electron-donating to electron-withdrawing) at the C-4 to 6 positions of α-hydroxy-1-indanones 1 participated in the cascade reactions to give the desired products 3n-3x in 62%-81% yields, 4.3:1-13:1 diastereoselectivities and 86%-96% enantioselectivities. Notably, the absolute configuration of the major isomer of product 3f was determined by the X-ray crystallographic analysis and that of other products was assigned by analogy[27].

Acyl transfer-enabled catalytic asymmetric Michael addition of <i>α</i>-hydroxy-1-indanones to nitroolefins

Scheme 3. Reaction scope. Reaction conditions: Unless otherwise noted, all reactions were conducted with 5 mol% of L4, 10 mol % of ZnEt2, 0.20 mmol 1 and 0.20 mmol 2 in 2 mL MeCN. Isolated yields. The diastereomeric ratio parameter of 3 was detected by 1H NMR of the crude reaction mixture. The enantiomeric excess (ee) value was determined by HPLC analysis.

To showcase the synthetic utility of this protocol, a gram-scale synthesis of 3f was carried out by using 5 mmol of 1a and 5 mmol of 2f. Under the standard condition, the reaction proceeded smoothly to give product 3f in 69% yield (1.48 g) with 10:1 dr and 93% ee [Scheme 4A]. Further reduction of nitro group with the NiCl2/NaBH4 system and hydrolysis of the ester group took place in one-pot and afforded the indeno[1,2-b]pyrrol-(3H)-ol derivative 5 [Scheme 4B].

Acyl transfer-enabled catalytic asymmetric Michael addition of <i>α</i>-hydroxy-1-indanones to nitroolefins

Scheme 4. Gram-scale reaction (A) and derivatization (B).

As previously described, a plausible reaction mechanism for this acyl transfer-enabled catalytic asymmetric Michael addition was illustrated in Scheme 5. Firstly, α-hydroxy-1-indanone 1a and nitroenone 2a were coordinated to the two zinc atoms in the chiral pocket of the dinuclear zinc complex in a less hindered manner. Then, the enantioselective Michael addition led to the intermediate B. Next, an intramolecular hemiketalization proceeded in the same chiral pocket to give intermediate C, which underwent the retro-Claisen reaction to afford the complex D. Finally, the catalytic cycle was restarted after a proton exchange of intermediate D with another α-hydroxy-1-indanone 1a, followed by the release of product 3a.

Acyl transfer-enabled catalytic asymmetric Michael addition of <i>α</i>-hydroxy-1-indanones to nitroolefins

Scheme 5. Proposed reaction mechanism.

DFT calculations were performed on the enantioselectivity-determining step to elucidate the origins of selectivity. Model catalyst IN1 [Figure 2] was used for the calculation. The ligand exchange of substrate 1a and ethane leads to IN2, which is exergonic by 21.5 kcal/mol, followed by the Michael addition step. Our calculations show that the pathway leading to the major RR-enantiomer (via transition state TS3-RR) has a free energy barrier of 13.8 kcal/mol, which is 2.3 kcal/mol more favorable than that leading to the minor SS-enantiomer (via transition state TS3-SS) and agrees with experiment. Detailed analyses indicate that there is favorable C-H…π interactions between the C-H bond adjacent to C1 in 1a and the phenyl ring connecting to C2 in 2a (2.69 Å, Figure 2) in TS3-RR. On the other hand, however, unfavorable steric repulsion was found between hydrogen atoms of the two substrates in TS3-SS (the closest H-H distance is 2.04 Å, Figure 2). The steric repulsion between the two substrates in TS3-SS would retard the C1-C2 bond formation, as manifested by the much longer C1-C2 distance in TS3-SS (2.29 Å) than in TS3-RR (2.16 Å). Thus, our computations reveal that both the C-H…π interaction in TS3-RR and the steric effect in TS3-SS account for the observed enantioselectivity.

Acyl transfer-enabled catalytic asymmetric Michael addition of <i>α</i>-hydroxy-1-indanones to nitroolefins

Figure 2. The calculated free energy profile and geometries of the key transition states for the enantioselectivity-determining Michael addition step (calculations were performed at the M06/6-311++G(d,p)/SDD//B3LYP-D3BJ/6-31G(d,p)/LANL2DZ//SMD(solvent=Acetonitrile) level of theory; bond distances are given in Å).

CONCLUSION

In conclusion, we have disclosed a novel acyl transfer-enabled catalytic asymmetric Michael reaction of α-hydroxy-1-indanones with nitroolefins via an underexplored electrophilic mode of activation. The chemical event underwent a reaction cascade of dinuclear zinc-catalyzed asymmetric Michael addition, intramolecular cyclization, and the retro-Claisen reaction. Good yields and stereoselectivities of the desired products were obtained with a wide substrate scope under mild conditions. In the activation mode, the dinuclear zinc complex acted as a bifunctional catalyst, wherein one zinc atom worked as a Lewis acid and the another functioned as a Brønsted base. Further applications of this catalytic asymmetric acyl transfer via electrophile activation for the synthesis of polyfunctional heterocycles are ongoing in our laboratory.

DECLARATIONS

Authors’ contributions

Designing the experiments, writing the manuscript, and being responsible for the whole work: Jia SK, Wang MC, Mei GJ

Performing the experiments: Xu ZH, Hua YZ

Synthesizing the substrates: Chang ZR

DFT calculations: Li N, Xu LP

Availability of data and materials

Supplementary materials are available online for this paper.

Financial support and sponsorship

Financial support from the Natural Science Foundation of Henan Province (222300420084, 222300420292), China Postdoctoral Science Foundation (2022M712862), application research plan of Key Scientific Research Projects in Colleges and Universities of Henan Province (22A150056), and Zhengzhou University (JC22261005) are gratefully acknowledged.

Conflicts of interest

All authors declared that there are no conflicts of interest.

Ethical approval and consent to participate

Not applicable.

Consent for publication

Not applicable.

Copyright

© The Author(s) 2023.

Supplementary Materials

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OAE Style

Xu ZH, Li N, Chang ZR, Hua YZ, Xu LP, Jia SK, Wang MC, Mei GJ. Acyl transfer-enabled catalytic asymmetric Michael addition of α-hydroxy-1-indanones to nitroolefins. Chem Synth 2023;3:17. http://dx.doi.org/10.20517/cs.2022.35

AMA Style

Xu ZH, Li N, Chang ZR, Hua YZ, Xu LP, Jia SK, Wang MC, Mei GJ. Acyl transfer-enabled catalytic asymmetric Michael addition of α-hydroxy-1-indanones to nitroolefins. Chemical Synthesis. 2023; 3(2): 17. http://dx.doi.org/10.20517/cs.2022.35

Chicago/Turabian Style

Xu, Zhi-Hua, Na Li, Zhe-Ran Chang, Yuan-Zhao Hua, Li-Ping Xu, Shi-Kun Jia, Min-Can Wang, Guang-Jian Mei. 2023. "Acyl transfer-enabled catalytic asymmetric Michael addition of α-hydroxy-1-indanones to nitroolefins" Chemical Synthesis. 3, no.2: 17. http://dx.doi.org/10.20517/cs.2022.35

ACS Style

Xu, Z.H.; Li N.; Chang Z.R.; Hua Y.Z.; Xu L.P.; Jia S.K.; Wang M.C.; Mei G.J. Acyl transfer-enabled catalytic asymmetric Michael addition of α-hydroxy-1-indanones to nitroolefins. Chem. Synth. 2023, 3, 17. http://dx.doi.org/10.20517/cs.2022.35

About This Article

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© The Author(s) 2023. Open Access This article is licensed under a Creative Commons Attribution 4.0 International License (https://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, sharing, adaptation, distribution and reproduction in any medium or format, for any purpose, even commercially, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made.

Author Biographies

Zhi-Hua Xu
Zhi-Hua Xu obtained his B.Sc. from Henan Institute of Science and Technology in 2019 and his master degree in organic chemistry from Zhengzhou University under the supervision of Prof. Min-Can Wang in 2022. He is currently a pharmacal synthesis researcher at Asymchem Laboratories Tianjin Co. Ltd.
Na Li
Na Li obtained her bachelor's degree from Shandong University of Technology in 2020. She is currently a master degree candidate with A/Prof. Li-Ping Xu at the School of Chemistry and Chemical Engineering, Shandong University of Technology. Her current research focuses on theoretical calculation of organic reactions catalyzed by transition metals and supramolecular metallocages.
Zhe-Ran Chang
Zhe-Ran Chang obtained her B.Sc. in Chemistry from Zhengzhou Normal University in 2020. She is currently degree candidate in organic chemistry with Prof. Min-Can Wang at Zhengzhou University. Her current scientific interest focuses on the Metal-organic asymmetric synthesis.
Yuan-Zhao Hua
Yuan-Zhao Hua received his BSc degree in chemistry from Zhengzhou University in 2005 and his PhD degree in organic chemistry from Zhengzhou University under the supervision of Prof. Jun-Biao Chang in 2015. He then joined Prof. Min-Can Wang’s group as a lecturer at Zhengzhou University. His current scientific interest focuses on the design and application of dinuclear zinc catalysts.
Li-Ping Xu
Li-Ping Xu obtained her B.Sc. in Chemistry from Shandong University in 2011 and his Ph.D. degree in physical chemistry from Peking University under the supervision of Prof. Yun-Dong Wu in 2016. He then joined Shandong University of Technology as an assistant professor. In 2019 to 2021, he was a postdoctoral researcher at Emory University under the supervision of Prof. Djamaladdin G. Musaev. He was promoted to associated professor in 2021. His research interests include the theoretical and computational study on tansition-metal and chiral phosphoric acid-catalyzed organic reactions.
Shi-Kun Jia
Shi-Kun Jia received his BSc degree in chemistry from Zhengzhou University in 2012 and his PhD degree in organic chemistry from East China Normal University under the supervision of Prof. Wenhao Hu in 2017. From 2017 to 2019, he was a postdoctoral researcher at Sun Yat-Sen University with Prof. Xianxing Jiang. He then joined Prof. Min-Can Wang's group as a lecturer at Zhengzhou University. His current scientific interest focuses on the catalytic asymmetric synthesis.
Min-Can Wang
Min-Can Wang obtained his bachelor degree from Henan Normal University in 1986 and his master degree in chemistry from Peking University under the supervision of Prof. Wen-Bao Chang in 1993. Then he started teaching in the Department of Chemistry, Zhengzhou University. He received his Ph.D. degree in Organic Chemistry under the supervision of Prof. De-Kun Wang from Zhengzhou University in 2004. In 2005, he was promoted to full professor of College of Chemistry, Zhengzhou University. Since then, his research interest focuses on the design and application of chiral catalysts.
Guang-Jian Mei
Guang-Jian Mei graduated from Zhengzhou University in 2011 and received his Ph.D. degree in Organic Chemistry under the supervision of Prof. Chuang-Chuang Li and Prof. Zhen Yang from Peking University in 2016. Then he joined the Jiangsu Normal University as an Associate Professor. From 2018 to 2021, he carried out his postdoctoral research with Prof. Yixin Lu at National University of Singapore. In 2021, he began an independent academic career at Zhengzhou University, where he is now a full professor. His current research interest focuses on asymmetric catalysis and natural product total synthesis.

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