Enantioselective protonation of catalytically generated chiral enolates as an approach to the synthesis of α-chloroesters
Enantioselective protonation of catalytically generated chiral enolates as an approach to the synthesis of α-chloroesters
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DOI：
10.1021/ja055918a
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发表时间：
2005-11-30
影响因子：
15
通讯作者：
Rovis, T
中科院分区：
文献类型：
--
作者：
Reynolds, NT;Rovis, T
在手性三唑盐催化剂和过量碱的存在下，用各种酚处理α，α-二氯醛，合成收率高、对映选择性好的α-氯芳基酯。该反应对醛的各种官能团以及几种电子不同的酚具有耐受性。产物氯酯进一步转化为氯酸、氯丙烷和叠氮酯，对映体选择性几乎完全保留。
Treatment of α,α-dichloroaldehydes with various phenols in the presence of chiral triazolium salt catalysts and excess base results in the synthesis of α-chloro aryl esters in good yield and enantioselectivity. The reaction is tolerant of various functionality on the aldehyde as well as several electronically diverse phenols. The product chloroesters were further transformed into chloroacid, chlorohydrin, and azidoesters with nearly complete retention of enantioselectivity.