Hydroxyl group-directed organocatalytic asymmetric Michael addition of alpha,beta-unsaturated ketones with alkenylboronic acids

Tsubasa Inokuma; Kiyosei Takasu; Toshiyuki Sakaeda; Yoshiji Takemoto

doi:10.1021/ol9006053

Hydroxyl group-directed organocatalytic asymmetric Michael addition of alpha,beta-unsaturated ketones with alkenylboronic acids

Org Lett. 2009 Jun 4;11(11):2425-8. doi: 10.1021/ol9006053.

Authors

Tsubasa Inokuma¹, Kiyosei Takasu, Toshiyuki Sakaeda, Yoshiji Takemoto

Affiliation

¹ Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501, Japan.

PMID: 19402642
DOI: 10.1021/ol9006053

Abstract

The organocatalytic asymmetric Michael addition of organoboronic acids to gamma-hydroxy enones in the presence of an iminophenol-type thiourea catalyst is demonstrated. The hydroxyl group in the substrates plays a critical role in this reaction.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkenes / chemical synthesis*
Alkenes / chemistry*
Boronic Acids / chemistry*
Catalysis
Ketones / chemical synthesis*
Ketones / chemistry*
Molecular Structure
Stereoisomerism
Thiourea / chemistry

Substances

Alkenes
Boronic Acids
Ketones
Thiourea