Kinetic Separation and Asymmetric Reactions of Norcaradiene Cycloadducts: Facilitated Access via H2O-Accelerated Cycloaddition

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• 作者：William D. Mackay ; Jeffrey S. Johnson
• 刊名：Organic Letters
• 出版年：2016
• 出版时间：February 5, 2016
• 年：2016
• 卷：18
• 期：3
• 页码：536-539
• 全文大小：386K
• ISSN：1523-7052

文摘

We exploit the Buchner reaction to access 1,2-disubstituted cyclohexadiene synthons (norcaradienes), which participate in Hb>2b>O-accelerated cycloaddition with dieneophiles to provide cyclopropyl-fused [2.2.2]-bicyclooctene derivatives in good yields. Regioisomeric mixtures can be kinetically separated by exploiting different reaction rates in Diels–Alder reactions. Meso-Diels–Alder products may be enantioselectively desymmetrized, providing highly substituted cyclohexanes with up to seven contiguous stereocenters.