Highly selective synthesis of enantiopure (S,E)-α,β-unsaturated γ-amino esters through a sequential reaction of ethyl dibromoacetate with α-amino aldehydes promoted by chromium dichloride

被引：9

作者：

Concellon, Jose M. ^{[1
]}

Mejica, Carmen ^{[1
]}

机构：

[1] Univ Oviedo, Dept Organ Chem, Fac Chem, E-33071 Oviedo, Spain

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2007年 / 2007卷 / 31期

关键词：

diastereoselectivity; chromium; asymmetric synthesis; amino esters; sequential reactions;

D O I：

10.1002/ejoc.200700515

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A sequential reaction of ethyl dibromoacetate with various enantiopure N,N-dibenzyl- or N-Boc-alpha-amino aldehydes (derived from natural a-amino acids), promoted by chromium dichloride, afforded optically active (S,E)-alpha,beta-unsaturated gamma-amino esters. The C=C double bond was generated with total or very high E-selectivity and the (S,E)-alpha,beta-unsaturated gamma-amino esters were obtained with complete enantiomeric purity, except from N-Boc-phenylalaninal (as determined by chiral HPLC). A mechanism is proposed to explain this transf orination. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007).

引用

页码：5250 / 5255

页数：6

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