A highly enantioselective Strecker reaction catalyzed by titanium-N-salicyl-β-aminoalcohol complexes

被引：73

作者：

Banphavichit, V ^{[1
]}

Mansawat, W ^{[1
]}

Bhanthumnavin, W ^{[1
]}

Vilaivan, T ^{[1
]}

机构：

[1] Chulalongkorn Univ, Fac Sci, Dept Chem, Organ Synthesis Res Unit, Bangkok 10330, Thailand

来源：

TETRAHEDRON | 2004年 / 60卷 / 46期

关键词：

asymmetric; catalyst; imine; hydrocyanation;

D O I：

10.1016/j.tet.2004.07.097

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

N-salicyl-beta-amino alcohols 1 were synthesized and evaluated as ligands for catalytic asymmetric Strecker reactions. N-Benzhydrylaldimines derived from aromatic and aliphatic aldehydes reacted with TMSCN in the presence of 10 mol% of Ti-1 complex to give the Strecker products in excellent yields and in up to >98% ee. The presence of a protic additive is essential to ensure good conversion and reaction rate. The reaction conditions are simple and the stereochemical outcome is predictable from the configuration of the ligands, both enantiomers of which are readily synthesized. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：10559 / 10568

页数：10

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