Organic Letters 2006-09-28

Rhodium-catalyzed asymmetric allylic substitution with boronic acid nucleophiles.

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

Index: Org. Lett. 8 , 4569, (2006)

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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.