Tetrahedron

Synthesis of 1, 3-dienes of (E, Z) configuration by a three-component coupling strategy

JD White, MS Jensen

Index: White, James D.; Jensen, Mark S. Tetrahedron, 1995 , vol. 51, # 20 p. 5743 - 5756

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Citation Number: 12

Abstract

Three-component coupling of an anionic nucleophile, butadienyltriphenylphosphonium bromide, and an aldehyde gave conjugated dienes of predominantly (E, Z) configuration. Dianions of β-dicarbonyl systems and dicarboxylic acids, and monoanions of sulfones were employed as nucleophiles. Stereoselectivity in favor of an (E, Z)-1, 3-diene was highest when a β-dicarbonyl dianion was used in conjunction with an α-branched aldehyde.