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

Rhodium-catalyzed asymmetric allylic substitution with boronic acid nucleophiles

Frederic Menard  1 , Timothy M Chapman, Chris Dockendorff, Mark Lautens
Affiliations

Rhodium-catalyzed asymmetric allylic substitution with boronic acid nucleophiles

Frederic Menard et al. Org Lett. .

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.

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