期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 70, 期 20, 页码 8035-8046出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo0511290
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资金
- NCI NIH HHS [CA103507] Funding Source: Medline
- NIGMS NIH HHS [GM038907] Funding Source: Medline
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.
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