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  • Rhodium-catalyzed asymmetric allylic substitution with boronic acid nucleophiles.

Rhodium-catalyzed asymmetric allylic substitution with boronic acid nucleophiles.

Organic letters (2006-09-22)
Frederic Menard, Timothy M Chapman, Chris Dockendorff, Mark Lautens
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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
4-(N-Boc-amino)phenylboronic acid, ≥95.0%
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