Issue 16, 2012
From the journal:

Organic & Biomolecular Chemistry

Highly enantioselective [4 + 2] cycloadditions of allenoates and dual activated olefins catalyzed by N-acyl aminophosphines†

Hua Xiao,a   Zhuo Chai,b   Dongdong Cao,a   Hongyu Wang,a   Jinghao Chenb  and  Gang Zhao*ab  

* Corresponding authors

a Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, P. R. China
E-mail: zhaog@mail.sioc.ac.cn
Fax: (+86) 21-64166128

b Laboratory of Modern Synthetic Chemistry, Shanghai Institute of Organic Chemistry, 354 Fenglin Road, Shanghai 200032, P. R. China

Abstract

An asymmetric organocatalytic [4 + 2] cycloaddition between α-substituted allenoates and dual activated olefins using bifunctional N-acyl aminophosphine catalysts is described. The use of 2-cyano acrylate derived olefins led to the first successful incorporation of an electrophile derived from an aliphatic aldehyde into this reaction.

Graphical abstract: Highly enantioselective [4 + 2] cycloadditions of allenoates and dual activated olefins catalyzed by N-acyl aminophosphines

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Article information

DOI
https://doi.org/10.1039/C2OB25295C
Article type
Paper
Submitted
09 Feb 2012
Accepted
23 Feb 2012
First published
14 Mar 2012

Org. Biomol. Chem., 2012,10, 3195-3201

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Highly enantioselective [4 + 2] cycloadditions of allenoates and dual activated olefins catalyzed by N-acyl aminophosphines

H. Xiao, Z. Chai, D. Cao, H. Wang, J. Chen and G. Zhao, Org. Biomol. Chem., 2012, 10, 3195 DOI: 10.1039/C2OB25295C

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