Bartoli Giuseppe, Bosco Marcella, Carlone Armando, Locatelli Manuela, Massaccesi Massimo, Melchiorre Paolo, Sambri Letizia
Department of Organic Chemistry A. Mangini, University of Bologna, v.le Risorgimento 4, 40136 Bologna, Italy.
Org Lett. 2004 Jun 24;6(13):2173-6. doi: 10.1021/ol049372t.
[reaction: see text] 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)Cl] 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.
[反应:见正文] 首次报道了反式芳族环氧化物与苯胺的不对称氨解反应。该过程可提供对映体富集的反式β-氨基醇,对映体过量率高达99%。所观察到的完全区域和非对映选择性使用市售的[Cr(Salen)Cl]作为路易斯酸催化剂,结合非常简单的实验步骤,使本反应成为合成手性非外消旋反式β-氨基醇的简便实用工具。