Enantioselective oxazaborolidinium-catalyzed Diels-Alder reactions without CH••••O hydrogen bonding
Enantioselective oxazaborolidinium-catalyzed Diels-Alder reactions without CH••••O hydrogen bonding
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DOI：
10.1002/anie.200802002
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发表时间：
2008-01-01
影响因子：
16.6
通讯作者：
Sherburn, Michael S.
中科院分区：
文献类型：
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作者：
Paddon-Row, Michael N.;Kwan, Laurence C. H.;Sherburn, Michael S.
（给出化学方程式）所有顺式都开始！对标题反应的首次详细计算研究验证了 Corey 的两个过渡态前模型，并揭示了第三种路易斯酸配位模式（见图），该模式适用于具有 s-cis C= CC= O 基团的酯。新的过渡态前模型解释了几个狄尔斯-阿尔德反应中意想不到的对映选择性，并且不涉及 CH⋯ O 氢键。
(Chemical Equation Presented) All cis-tems go! The first detailed computational investigations into the title reaction validate Corey's two pre-transition-state models and reveal a third Lewis acid coordination mode (see picture), which operates for esters having s-cis C= CC= O groups. The new pre-transition-state model explains the unexpected enantioselectivity witnessed for several Diels-Alder reactions and does not involve a CH⋯ O hydrogen bond.