Enantio- and diastereo-selective reaction of but-2-enylstannane with glyoxylate esters and its application to a short synthesis of verrucarinolactone

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Abstract
The erythro-3-alkyl-2-hydroxypropionate unit in (4) is predominantly obtained via the reaction of but-2-enylstannane (2a) with glyoxylate esters (3) while the threo-isomer (5) is preferentially produced via 9-but-2-enyl-9-borabicyclo[3.3.1] nonane (2b); the former reaction has been applied to the enantioselective synthesis of verrucarinolactone (6).