Stereoselective Synthesis of 4-oxo-2,5-dienes and conjugated dienes by Stille cross coupling reactions of vinylstannanes

PABLO M. FIDELIBUS; DARÍO C. GERBINO; SANDRA D. MANDOLESI; JULIO C. PODESTÁ

Arkivoc

ARKAT USA Inc

Lugar: Florida; Año: 2007 vol. iv p. 389 - 396

1424-6376

The palladium-catalyzed cross coupling reactions between trineophylstannylvinyl esters and unsaturated acyl chlorides lead mostly to 4-oxo-2,5-dienes in good yields (60-77%). In some cases homocoupling products are also formed. On the other hand, the Stille reaction of Z-di- and trisubstituted vinyl iodides with trineophylvinylstannanes enables the synthesis of polysubstituted butadienes in moderate to good yields (40-60%). Keywords: Vinyltrineophylstannanes, unsaturated acyl chlorides, Stille reaction, 4-oxo-2,5- dienes, polysubstituted butadienes: Vinyltrineophylstannanes, unsaturated acyl chlorides, Stille reaction, 4-oxo-2,5- dienes, polysubstituted butadienes