Oxidative Heck Vinylation for the Synthesis of Complex Dienes and Polyenes

JH Delcamp, PE Gormisky…

Index: Delcamp, Jared H.; Gormisky, Paul E.; White, M. Christina Journal of the American Chemical Society, 2013 , vol. 135, # 23 p. 8460 - 8463

Full Text: HTML

Citation Number: 33

Abstract

We introduce an oxidative Heck reaction for selective complex diene and polyene formation. The reaction proceeds via oxidative Pd (II)/sulfoxide catalysis that retards palladium-hydride isomerizations which previously limited the Heck manifold's capacity for furnishing stereodefined conjugated dienes. Limiting quantities of nonactivated terminal olefins (1 equiv) and slight excesses of vinyl boronic esters (1.5 equiv) that feature diverse ...

Related Articles:

Pheromone synthesis. Part 244: Synthesis of the racemate and enantiomers of (11Z, 19Z)-CH503 (3-acetoxy-11, 19-octacosadien-1-ol), a new sex pheromone of male …

[Mori, Kenji; Shikichi, Yasumasa; Shankar, Shruti; Yew, Joanne Y. Tetrahedron, 2010 , vol. 66, # 35 p. 7161 - 7168]

Total Synthesis of Umuravumbolide and Hyptolide Through Silicon??Tethered Ring??Closing Metathesis

[Chowdhury, Partha Sarathi; Kumar, Pradeep European Journal of Organic Chemistry, 2013 , # 21 p. 4586 - 4593]

Enantioselective synthesis of a putative hexaketide intermediate in the biosynthesis of the squalestatins

[Simpson, Thomas J.; Smith, Robert W.; Westaway, Susan M.; Willis, Christine L.; Buss, Antony D.; Cannell, Richard J. P.; Dawson, Michael J.; Rudd, Brian A. M. Tetrahedron Letters, 1997 , vol. 38, # 30 p. 5367 - 5370]

More Articles...