Enantioselective addition of methyllithium to a prochiral imine - the substrate in the Pomeranz-Fritsch-Bobbitt synthesis of tetrahydroisoquinoline derivatives mediated by chiral monooxazolines

被引：12

作者：

Gluszynska, A ^{[1
]}

Rozwadowska, MD ^{[1
]}

机构：

[1] Adam Mickiewicz Univ Poznan, Fac Chem, PL-60780 Poznan, Poland

来源：

TETRAHEDRON-ASYMMETRY | 2004年 / 15卷 / 20期

关键词：

D O I：

10.1016/j.tetasy.2004.08.011

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A series of chiral monooxazoline ligands 7-24 with substituents at C-2 and C-4, differing in electronic and steric properties, has been synthesized from (+)-thiomicamine 6. The effect of the oxazoline structure on the course of addition of methyllithium to imine 1 has been studied. The addition product, amine 3, which is the key intermediate in the Pomeranz-Fritsch-Bobbitt synthesis of tetrahydroisoquinoline derivatives, has been obtained in high yield (92%) and with up to 76% ee. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：3289 / 3295

页数：7

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