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. 2013 Oct 11;52(42):11114-8.
doi: 10.1002/anie.201305492. Epub 2013 Aug 27.

A powerful hydrogen-bond-donating organocatalyst for the enantioselective intramolecular oxa-Michael reaction of α,β-unsaturated amides and esters

Yusuke Kobayashi  1 , Yamato Taniguchi, Noboru Hayama, Tsubasa Inokuma, Yoshiji Takemoto
Affiliations

A powerful hydrogen-bond-donating organocatalyst for the enantioselective intramolecular oxa-Michael reaction of α,β-unsaturated amides and esters

Yusuke Kobayashi et al. Angew Chem Int Ed Engl. .

Abstract

Tuning the organocatalyst: An unprecedented enantioselective intramolecular oxa-Michael reaction of unactivated α,β-unsaturated amides and esters catalyzed by a powerful hydrogen-bond-donating organocatalyst has been developed. Furthermore, the products obtained from this reaction have been used for the straightforward asymmetric synthesis of several natural products and biologically important compounds.

Keywords: Michael reaction; asymmetric synthesis; heterocycles; hydrogen bonding; stereoselective catalysis.

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