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. 2010 Aug 20;75(16):5580-9.
doi: 10.1021/jo1008959.

Palladium-catalyzed synthesis of enantiomerically pure alpha-substituted allylboronic esters and their addition to aldehydes

Enrique Fernández  1 , Jörg Pietruszka, Wolfgang Frey
Affiliations

Palladium-catalyzed synthesis of enantiomerically pure alpha-substituted allylboronic esters and their addition to aldehydes

Enrique Fernández et al. J Org Chem. .

Abstract

Tartrate-derived boronic esters 2 can be subjected to palladium-catalyzed carbonyl allylations with SnCl(2) to obtain enantiomerically pure alpha-substituted allylboronic esters 8 and 9. The reaction proceeds regioselectively and with high, simple diastereoselectivity to form anti-products. Their addition to aldehydes yields enantiomerically enriched homoallylic alcohols 17 and 18, respectively. Synthesis, characterization, and a mechanistic rational is presented here.

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