Asymmetric rearrangement of N-Boc 7-azanorbornene oxide:: use of aryllithiums for enantioselective deprotonation

被引：25

作者：

Hodgson, DM

Maxwell, CR

Matthews, IR

机构：

[1] Univ Oxford, Dyson Perrins Lab, Dept Chem, Oxford OX1 3QY, England

[2] Zeneca Agrochem, Jealotts Hill Res Stn, Bracknell RG42 6ET, Berks, England

来源：

TETRAHEDRON-ASYMMETRY | 1999年 / 10卷 / 10期

基金：

英国工程与自然科学研究理事会;

关键词：

D O I：

10.1016/S0957-4166(99)00168-8

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The enantioselective alpha-deprotonation-rearrangement of N-Boc 7-azanorbornene oxide 1 using aryllithiums in the presence of (-)-sparteine 4 or bisoxazolines 5a-c to give azanortricyclanol 2 in up to 87% ee is described. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：1847 / 1850

页数：4

共 13 条

[11] Aggregation and reactivity of phenyllithium solutions
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Phillips, NH
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (29) : 7201 - 7210
[12] Design, synthesis, and application of a C2 symmetric chiral ligand for enantioselective conjugate addition of organolithium to α,β-unsaturated aldimine
Shindo, M
Koga, K
Tomioka, K
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (25) : 9351 - 9357
[13] Enantioselective 1,4-addition of aryllithium reagents to α,β-unsaturated tert-butyl esters in the presence of chiral additives
Xu, F
Tillyer, RD
Tschaen, DM
Grabowski, EJJ
Reider, PJ
[J]. TETRAHEDRON-ASYMMETRY, 1998, 9 (10) : 1651 - 1655

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