Issue 42, 2012
From the journal:

Chemical Communications

Catalytic enantioselective construction of quaternary stereocenters by direct vinylogous Michael addition of deconjugated butenolides to nitroolefins†

Madhu Sudan Manna,a   Vikas Kumara  and  Santanu Mukherjee*a  

* Corresponding authors

a Department of Organic Chemistry, Indian Institute of Science, Bangalore 560 012, India
E-mail: sm@orgchem.iisc.ernet.in
Fax: +91-80-2360-0529
Tel: +91-80-2293-2850

Abstract

A direct vinylogous Michael reaction of γ-substituted deconjugated butenolides with nitroolefins has been developed with the help of a newly identified quinine-derived bifunctional catalyst, allowing the synthesis of densely functionalized products with contiguous quaternary and tertiary stereocenters in excellent yield with perfect diastereoselectivity (>20 : 1 dr) and high enantioselectivity (up to 99 : 1 er).

Graphical abstract: Catalytic enantioselective construction of quaternary stereocenters by direct vinylogous Michael addition of deconjugated butenolides to nitroolefins

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Article information

DOI
https://doi.org/10.1039/C2CC31700A
Article type
Communication
Submitted
07 Mar 2012
Accepted
28 Mar 2012
First published
28 Mar 2012

Chem. Commun., 2012,48, 5193-5195

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Catalytic enantioselective construction of quaternary stereocenters by direct vinylogous Michael addition of deconjugated butenolides to nitroolefins

M. S. Manna, V. Kumar and S. Mukherjee, Chem. Commun., 2012, 48, 5193 DOI: 10.1039/C2CC31700A

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