Efficient resolution of N-Boc-7-azabicyclo[2.2.1]hept-5-en-2-one:: formal syntheses of natural epibatidine and its enantiomer

被引：21

作者：

Moreno-Vargas, AJ ^{[1
]}

Vogel, P ^{[1
]}

机构：

[1] Ecole Polytech Fed Lausanne, Inst Chim Mol & Biol, BCH, CH-1015 Lausanne, Switzerland

来源：

TETRAHEDRON-ASYMMETRY | 2003年 / 14卷 / 20期

关键词：

D O I：

10.1016/j.tetasy.2003.08.021

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The efficient resolution of racemic N-Boc-7-azabicyclo[2.2.1]hept-5-en-2-one (+/-)-2 via aminal formation with (R,R)-1,2-diphenylethylenediamine 4 is reported. Acidic hydrolysis furnishes the enantiomeric ketones (+)-2 and (-)-2 that were transformed into 7-azabicyclo[2.2.1]heptan-2-one (-)-3 and (+)-3. The process constitutes a formal synthesis of (+)- and (-)-epibatidine. (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：3173 / 3176

页数：4

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