On the scope, mechanism and stereochemistry of the Lewis acid catalyzed cyclocondensation of activated dienes with aldehydes: an application to the erythronolide …

S Danishefsky, E Larson, D Askin…

文献索引：Danishevsky,S.J.; Larson,E.; Askin,D. Journal of the American Chemical Society, 1985 , vol. 107, p. 1246

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被引用次数: 172

摘要

Abstract: The scope of the titled reaction is described. Pericyclic and aldol-like pathways have been identified. To a great extent these are a function of the catalyst/solvent system and of structural features in the aldehyde. The pericyclic pathway tends to favor a topology leading to cis-2, 3-dihydropyran. A complementary threo-selective siloxonium (aldol-like) pathway is favored by borontrifluoride catalysis. These capabilities are coordinated in a ...