Issue 42, 2012

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

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

Associated articles

Supplementary files

Article information

Article type
Communication
Submitted
07 mar 2012
Accepted
28 mar 2012
First published
28 mar 2012

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

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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