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

[11] ASYMMETRIC CREATION OF QUATERNARY CARBON CENTERS
FUJI, K
[J]. CHEMICAL REVIEWS, 1993, 93 (06) : 2037 - 2066
[12] Studies aimed at the total synthesis of azadirachtin. A modeled connection of C-8 and C-14 in azadirachtin
Fukuzaki, T
Kobayashi, S
Hibi, T
Ikuma, Y
Ishihara, J
Kanoh, N
Murai, A
[J]. ORGANIC LETTERS, 2002, 4 (17) : 2877 - 2880
[13] Recent advances in olefin metathesis and its application in organic synthesis
Grubbs, RH
Chang, S
[J]. TETRAHEDRON, 1998, 54 (18) : 4413 - 4450
[14] Enantioselective total synthesis of aspidophytine
He, F
Bo, YX
Altom, JD
Corey, EJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (28) : 6771 - 6772
[15] STEREOCHEMICAL CONTROL IN THE ESTER ENOLATE CLAISEN REARRANGEMENT .2. CHAIRLIKE VS BOATLIKE TRANSITION-STATE SELECTION
IRELAND, RE
WIPF, P
XIANG, JN
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (11) : 3572 - 3582
[16] Origins of boat or chair preferences in the Ireland-Claisen rearrangements of cyclohexenyl esters: A theoretical study
Khaledy, MM
Kalani, MYS
Khuong, KS
Houk, KN
Aviyente, V
Neier, R
Soldermann, N
Velker, J
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (02) : 572 - 577
[17] LADOUCEUR G, 1992, SYNTHESIS-STUTTGART, P185
[18] Stereocontrolled synthesis of spirocyclics
Sannigrahi, M
[J]. TETRAHEDRON, 1999, 55 (30) : 9007 - 9071
[19] Chiral synthons from carvone .25. Enantiospecific synthesis of (+)-dihydroerythrodiene, (+)-dihydrospirojatamol and (+)-dihydroepispirojatamol
Srikrishna, A
Vijaykumar, D
Reddy, TJ
[J]. TETRAHEDRON, 1997, 53 (04) : 1439 - 1446

← 1 2 →