[3 + 2]-annulation reactions of chiral allylsilanes and chiral aldehydes. studies on the synthesis of bis-tetrahydrofuran substructures of annonaceous acetogenins.
[3 + 2]-annulation reactions of chiral allylsilanes and chiral aldehydes. studies on the synthesis of bis-tetrahydrofuran substructures of annonaceous acetogenins.
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DOI：
10.1021/jo0511290
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发表时间：
2005-08
期刊：
影响因子：
--
通讯作者：
E. Mertz;J. M. Tinsley;W. Roush
中科院分区：
文献类型：
--
作者：
E. Mertz;J. M. Tinsley;W. Roush
[结构：见正文] 研究了手性 β-甲硅烷氧基烯丙基硅烷与手性 2-四氢呋喃基甲醛的双不对称 [3 + 2]-环化反应，从而立体控制合成了六种非对映异构双四氢呋喃结构，对应于番荔枝苷家族成员的核心亚基 天然产品。提出过渡态模型来解释双立体分化的[3 + 2]-环化反应的立体选择性。
[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.