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Xu et al. Chem Synth 2023;3:17 Chemical Synthesis
DOI: 10.20517/cs.2022.35

Research Article Open Access

Acyl transfer-enabled catalytic asymmetric Michael

addition of α-hydroxy-1-indanones to nitroolefins

2
1
1,*
1,*
2,*
1
1
Zhi-Hua Xu , Na Li , Zhe-Ran Chang , Yuan-Zhao Hua , Li-Ping Xu , Shi-Kun Jia , Min-Can Wang ,
Guang-Jian Mei 1,*
1
Green Catalysis Center, and College of Chemistry, Zhengzhou University, Zhengzhou 450001, Henan, China.
2
School of Chemistry and Chemical Engineering, Shandong University of Technology, Zibo 255000, Shandong, China.
*Correspondence to: Prof. Guang-Jian Mei, Green Catalysis Center, and College of Chemistry, Zhengzhou University, No. 100,
Kexue Avenue, Zhengzhou 450001, Henan, China. E-mail: meigj@zzu.edu.cn; Prof. Shi-Kun Jia, Green Catalysis Center, and
College of Chemistry, Zhengzhou University, No. 100, Kexue Avenue, Zhengzhou 450001, China. E-mail: jiashikun@zzu.edu.cn;
Prof. Min-Can Wang, Green Catalysis Center, and College of Chemistry, Zhengzhou University, No. 100, Kexue Avenue,
Zhengzhou 450001, China. E-mail: wangmincan@zzu.edu.cn; Prof. Li-Ping Xu, School of Chemistry and Chemical Engineering,
Shandong University of Technology, No. 266 West Xincun Road, Zibo, 255000, Shandong, China. E-mail: xulp@sdut.edu.cn
How to cite this article: Xu ZH, Li N, Chang ZR, Hua YZ, Xu LP, Jia SK, Wang MC, Mei GJ. Acyl transfer-enabled catalytic
asymmetric Michael addition of -hydroxy-1-indanones to nitroolefins. Chem Synth 2023;3:17.
https://dx.doi.org/10.20517/cs.2022.35
Received: 15 Nov 2022 First Decision: 4 Jan 2023 Revised: 17 Jan 2023 Accepted: 13 Mar 2023 Published: 24 Mar 2023

Academic Editor: Bao-Lian Su Copy Editor: Yanbin Bai Production Editor: Yanbin Bai

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, -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 . In order to circumvent
[2]

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