doi: 10.1021/jo1008959.
Palladium-catalyzed synthesis of enantiomerically pure alpha-substituted allylboronic esters and their addition to aldehydes
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- PMID: 20672807
- DOI: 10.1021/jo1008959
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Palladium-catalyzed synthesis of enantiomerically pure alpha-substituted allylboronic esters and their addition to aldehydes
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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