Issue 81, 2013
From the journal:

Chemical Communications

Organocatalyzed asymmetric vinylogous Michael addition of α,β-unsaturated γ-butyrolactam†

Jinlong Zhang,a   Xihong Liu,a   Xiaojuan Maa  and  Rui Wang*a  

* Corresponding authors

a Key Laboratory of Preclinical Study for New Drugs of Gansu Province, School of Basic Medical Sciences, Lanzhou University, Lanzhou, China
E-mail: wangrui@lzu.edu.cn

Abstract

Highly efficient asymmetric vinylogous 1,6-Michael addition of α,β-unsaturated γ-butyrolactam to 3-methyl-4-nitro-5-alkenyl-isoxazoles and Michael addition to trichloromethyl ketones by using a chiral quinine-derived squaramide organocatalyst were described, giving products with high diastereo- and enantioselectivities (up to >25 : 1 dr and 96% ee).

Graphical abstract: Organocatalyzed asymmetric vinylogous Michael addition of α,β-unsaturated γ-butyrolactam

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Article information

DOI
https://doi.org/10.1039/C3CC44059A
Article type
Communication
Submitted
30 May 2013
Accepted
15 Aug 2013
First published
15 Aug 2013

Chem. Commun., 2013,49, 9329-9331

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Organocatalyzed asymmetric vinylogous Michael addition of α,β-unsaturated γ-butyrolactam

J. Zhang, X. Liu, X. Ma and R. Wang, Chem. Commun., 2013, 49, 9329 DOI: 10.1039/C3CC44059A

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