A sequential Claisen/ring-closing metathesis approach to the synthesis of spirocyclic cyclopentanes and cyclohexanes

被引：15

作者：

Beaulieu, P ^{[1
]}

Ogilvie, WW ^{[1
]}

机构：

[1] Univ Ottawa, Dept Chem, Ottawa, ON K1N 6N5, Canada

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 49期

基金：

加拿大创新基金会; 加拿大自然科学与工程研究理事会;

关键词：

D O I：

10.1016/j.tetlet.2003.09.190

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new method for the formation of spirocycles is described using a sequential Ireland-Claisen/Metathesis strategy to construct spirocyclic systems. Optimization of the Ireland-Claisen conditions provides the key metathesis substrates. The metathesis reactions were highly regioselective by virtue of steric hindrance in the substrate olefins. (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：8883 / 8885

页数：3

共 19 条

[1] EVALUATION OF THE CLAISEN REARRANGEMENT OF 2-CYCLOHEXENOLS FOR THE STEREOSELECTIVE CONSTRUCTION OF A TERPENE SYNTHON
BARTLETT, PA
PIZZO, CF
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (19) : 3896 - 3900
[2] BURKE SD, 1981, J ORG CHEM, V46, P2400, DOI 10.1021/jo00324a041
[3] New aspects of the Ireland and related Claisen rearrangements
Chai, YH
Hong, SP
Lindsay, HA
McFarland, C
McIntosh, MC
[J]. TETRAHEDRON, 2002, 58 (15) : 2905 - 2928
[4] Christoffers J, 2001, ANGEW CHEM INT EDIT, V40, P4591, DOI 10.1002/1521-3773(20011217)40:24<4591::AID-ANIE4591>3.0.CO
[5] 2-V
[6] Corey EJ, 1998, ANGEW CHEM INT EDIT, V37, P1987, DOI 10.1002/(SICI)1521-3773(19980817)37:15<1986::AID-ANIE1986>3.0.CO
[7] 2-Z
[8] Corey EJ, 1998, ANGEW CHEM INT EDIT, V37, P388, DOI 10.1002/(SICI)1521-3773(19980302)37:4<388::AID-ANIE388>3.0.CO
[9] 2-V
[10] SERIAL RADICAL CYCLIZATION OF BRANCHED CARBOHYDRATES .1. SIMPLE PYRANOSIDE DIQUINANES
DICKSON, JK
TSANG, R
LLERA, JM
FRASERREID, B
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (22) : 5350 - 5356

← 1 2 →