[3 + 2]-annulation reactions of chiral allylsilanes and chiral aldehydes. Studies on the synthesis of bis-tetrahydrofuran substructures of annonaceous acetogenins

Academic Article
uri icon

publication date

  • September 2005

abstract

  • [Structure: See text] Double asymmetric [3 + 2]-annulation reactions of chiral beta-silyloxyallylsilanes with chiral 2-tetrahydrofuranyl carboxaldehydes have been studied, leading to the stereocontrolled synthesis of six diastereomeric bis-tetrahydrofuran structures corresponding to the core subunits of members of the Annonaceous acetogenin family of natural products. Transition-state models are proposed to account for the stereoselectivity of the double-stereodifferentiating [3 + 2]-annulation reactions.