Palladium-catalyzed conversion of β, γ-unsaturated silyl sulfinates into (E)-alkenes: asymmetric synthesis of polypropionate fragments
X Huang, C Craita, P Vogel
Index: Huang, Xiaogen; Craita, Cotinica; Vogel, Pierre Journal of Organic Chemistry, 2004 , vol. 69, # 12 p. 4272 - 4275
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Citation Number: 26
Abstract
At low temperature, 1-alkoxy-1, 3-dienes add to sulfur dioxide activated by a Lewis or protic acid generating zwitterionic intermediates that can be quenched by enoxysilanes. The resulting β, γ-unsaturated silyl sulfinates can be desilylated by 1: 1 Pd (OAc) 2/PPh3 catalyst, liberating the corresponding β, γ-unsaturated sulfinic acids that undergo smooth and highly stereoselective retro-ene eliminations of sulfur dioxide. The method has been applied to ...
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