Stereocontrolled palladium-catalysed umpolung allylation of aldehydes with allyl acetates

authored by

Monika Vogt, Sascha Ceylan, Andreas Kirschning

Abstract

In the present work the stereocontrolled palladium-catalysed umpolung allylation of aldehydes is described. Allyl acetates are in situ transformed into the corresponding allyl boronates, which directly react with aldehydes. The question of stereocontrol is raised by employing (a) chiral boronating agents (reagent control) and by (b) utilising chiral aldehydes (substrate control). These studies reveal that the approach based on substrate control is superior to the former one with respect to yields and stereoselectivity. Remarkably, this umpolung protocol often yields the 4,5-syn products in high selectivity, which is unprecedented for direct crotylations.

Organisation(s)

Institute of Organic Chemistry
Centre of Biomolecular Drug Research (BMWZ)

Type

Article

Journal

Tetrahedron

Volume

66

Pages

6450-6456

No. of pages

7

ISSN

0040-4020

Publication date

06.05.2010

Publication status

Published

Peer reviewed

Yes

ASJC Scopus subject areas

Biochemistry, Drug Discovery, Organic Chemistry

Electronic version(s)

https://doi.org/10.1016/j.tet.2010.04.133 (Access: Unknown)