Highly enantioselective desymmetrization of prochiral cyclic α,α-dicyanoalkenes via the direct vinylogous Michael/cyclization domino reaction

Author:

Mei Hongjiang12345ORCID,Lin Lili12345ORCID,Shen Bin12345ORCID,Liu Xiaohua12345ORCID,Feng Xiaoming12345ORCID

Affiliation:

1. Key Laboratory of Green Chemistry & Technology

2. Ministry of Education

3. College of Chemistry

4. Sichuan University

5. Chengdu 610064

Abstract

A chiral N,N′-dioxide/Mg(ii) complex efficiently constructs spiroindolinones which include three adjacent atom chiralities and a tertiary carbon center at remote sites in up to 95% yield, with 99% ee and 20 : 1 dr.

Funder

National Natural Science Foundation of China

Publisher

Royal Society of Chemistry (RSC)

Subject

Organic Chemistry

Reference41 articles.

1. Asymmetric Deprotonations Using Chiral Lithium Amide Bases , in Stereochemical Aspects of Organolithium Compounds , ed. R. E. Gawley , N. S. Simpkins and M. D. Weller , 2010 , ch. 1

2. Enantioselective desymmetrisation

3. Asymmetric Alcoholysis of Cyclic Anhydrides

4. Recent progress on asymmetric organocatalytic construction of chiral cyclohexenone skeletons

5. Organocatalytic enantioselective desymmetrisation

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