General, robust, and stereocomplementary preparation of alpha,beta-disubstituted alpha,beta-unsaturated esters

Hidefumi Nakatsuji; Hiroshi Nishikado; Kanako Ueno; Yoo Tanabe

doi:10.1021/ol9013359

General, robust, and stereocomplementary preparation of alpha,beta-disubstituted alpha,beta-unsaturated esters

Org Lett. 2009 Oct 1;11(19):4258-61. doi: 10.1021/ol9013359.

Authors

Hidefumi Nakatsuji¹, Hiroshi Nishikado, Kanako Ueno, Yoo Tanabe

Affiliation

¹ Department of Chemistry, School of Science and Technology, Kwansei Gakuin University, 2-1 Gakuen, Sanda, Hyogo 669-1337, Japan.

PMID: 19715286
DOI: 10.1021/ol9013359

Abstract

An (E)- and (Z)-stereocomplementary preparative method for alpha,beta-disubstituted alpha,beta-unsaturated esters is performed via three general and robust reaction sequences: (i) Ti-Claisen condensation (formylation) of esters to give alpha-formyl esters (12 examples, 60-99%), (ii) (E)- and (Z)-stereocomplementary enol p-toluenesulfonylation (tosylation) using TsCl-N-methylimidazole (NMI)-Et(3)N and LiOH (24 examples, 82-99%), and (iii) stereoretentive Suzuki-Miyaura cross-coupling (18 examples, 64-96%).

Publication types

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

MeSH terms

Esters / chemical synthesis*
Esters / chemistry*
Molecular Structure
Stereoisomerism

Substances

Esters