Rhodium-catalyzed asymmetric allylic substitution with boronic acid nucleophiles

Frederic Menard; Timothy M Chapman; Chris Dockendorff; Mark Lautens

doi:10.1021/ol061777l

Rhodium-catalyzed asymmetric allylic substitution with boronic acid nucleophiles

Org Lett. 2006 Sep 28;8(20):4569-72. doi: 10.1021/ol061777l.

Authors

Frederic Menard¹, Timothy M Chapman, Chris Dockendorff, Mark Lautens

Affiliation

¹ Davenport Laboratories, Department of Chemistry, University of Toronto, Toronto, Ontario, Canada M5H 3H6.

PMID: 16986952
DOI: 10.1021/ol061777l

Abstract

An enantio-, regio-, and diastereoselective rhodium(I)-catalyzed desymmetrization of a meso-cyclic allylic dicarbonate with organoboronic acid nucleophiles is described. The rhodium(I) catalyst formed in situ from [Rh(cod)OH]2 and Xyl-P-PHOS allowed the S(N)2' allylic substitution product to be obtained with a range of arylboronic acids in enantiomeric excesses of up to 92% with regioselectivities of up to >20:1.

Publication types

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

MeSH terms

Boronic Acids / chemistry*
Catalysis
Rhodium / chemistry*

Substances

Boronic Acids
Rhodium