Stereoselective Synthesis of γ-Substituted (Z)-Allylic Boranes via Kinetically Controlled Hydroboration of Allenes with 10-TMS-9-borabicyclo[3.3.2]decane

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• 作者：Jeremy Kister ; Amy C. DeBaillie ; Ricardo Lira ; William R. Roush
• 刊名：Journal of the American Chemical Society
• 出版年：2009
• 出版时间：October 14, 2009
• 年：2009
• 卷：131
• 期：40
• 页码：14174-14175
• 全文大小：166K
• 年卷期：v.131,no.40(October 14, 2009)
• ISSN：1520-5126

文摘

Kinetically controlled hydroboration of allenes 8 and 14a−d with the readily accessible Soderquist borane 7, which is generated in situ from borohydride 6, constitutes a convenient and preparatively useful method for synthesis of (Z)-γ-(substituted)allylboranes 9 and 15a−d. These allylboranes undergo highly diastereo- (≥90: 10) and enantioselective (typically 89−96% e.e.) allylboration reactions with representative aldehydes to give syn-β-functionalized homoallylic alcohols.