Asymmetric aminolysis of aromatic epoxides:: A facile catalytic enantioselective synthesis of anti-β-amino alcohols

被引:113
作者
Bartoli, G [1 ]
Bosco, M [1 ]
Carlone, A [1 ]
Locatelli, M [1 ]
Massaccesi, M [1 ]
Melchiorre, P [1 ]
Sambri, L [1 ]
机构
[1] Univ Bologna, Dept Organ Chem A Mangini, I-40136 Bologna, Italy
关键词
D O I
10.1021/ol049372t
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first asymmetric aminolysis of trans-aromatic epoxides with anilines is described. The process affords enantioenriched anti-beta-amino alcohols in up to 99% ee. The complete regio- and diastereoselectivity observed uses commercially available [Cr(Salen)CI] as a Lewis acid catalyst and in combination with a very simple experimental procedure renders the present reaction a facile and practical tool for the synthesis of chiral nonracemic anti-beta-amino alcohols.
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页码:2173 / 2176
页数:4
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