Catalytic asymmetric rearrangement of allylic trichloroacetimidates. A practical method for preparing allylic amines and congeners of high enantiomeric purity
Catalytic asymmetric rearrangement of allylic trichloroacetimidates. A practical method for preparing allylic amines and congeners of high enantiomeric purity
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DOI：
10.1021/ja037086r
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发表时间：
2003-10-15
影响因子：
15
通讯作者：
Overman, LE
中科院分区：
文献类型：
--
作者：
Anderson, CE;Overman, LE
COP−Cl 催化 (E)-烯丙基三氯乙酰亚胺酯的重排，提供高对映体纯度的转位烯丙基三氯乙酰胺，这一转化是第一个真正实用的方法，用于将前手性烯丙醇转化为对映体富集的烯丙胺和同系物。这种不对称重排的高官能团相容性以及在烯丙基三氯乙酰亚胺酯到烯丙基三氯乙酰胺转化的合成中所表现出的广泛用途是这种新的催化不对称反应的独特特征。
COP−Cl catalyzes the rearrangement of (E)-allylic trichloroacetimidates to provide transposed allylic trichloroacetamides of high enantiopurity, a transformation that underlies the first truly practical method for transforming prochiral allylic alcohols to enantioenriched allylic amines and congeners. The high functional group compatibility of this asymmetric rearrangement and the demonstrated broad utility in synthesis of the allylic trichloroacetimidate to allylic trichloroacetamide conversion are singular features of this new catalytic asymmetric reaction.