Allylboronic acids are synthetically very useful building blocks for chemical transformations. Recently we have reported that allylboronic acids react directly (without additives) with ketones1 and imines2,3 under mild conditions. The reaction is highly regio- and stereoselective. Now we have developed4 the catalytic asymmetric allylboration of ketones using allylboronic acids and BINOL derivatives. This reaction gives easy access to synthesize homoallylic alcohols bearing two adjacent quaternary stereocenters with high enantiomeric access (Scheme 01).

Enantioselective synthesis of contiguous quaternary stereocenters by organocatalytic allylboration

251st National Meeting (2016)

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