Olefin isomerization by a ruthenium carbenoid complex. Cleavage of allyl and homoallyl groups

被引：115

作者：

Cadot, C ^{[1
]}

Dalko, PI ^{[1
]}

Cossy, J ^{[1
]}

机构：

[1] ESPCI, CNRS, Chim Organ Lab, F-750231 Paris 05, France

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 10期

关键词：

alkenes; isomerization; protecting groups;

D O I：

10.1016/S0040-4039(02)00141-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Ruthenium-carbenoid catalysts such as Grubbs' complex I mediate efficiently the isomerization of beta,gamma-unsaturated ethers and amines to the corresponding vinyl ethers and enamines. This reaction can be useful in the deprotection of allyl and homoallyl ethers as well as amines. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：1839 / 1841

页数：3

共 57 条

[1] A novel use of Grubbs' carbene. Application to the catalytic deprotection of tertiary allylamines
Alcaide, B
Almendros, P
Alonso, JM
Aly, MF
[J]. ORGANIC LETTERS, 2001, 3 (23) : 3781 - 3784
[2] RUTHENIUM-CATALYZED ISOMERIZATION OF ALLYLIC ALCOHOLS TO SATURATED KETONES
BACKVALL, JE
ANDREASSON, U
[J]. TETRAHEDRON LETTERS, 1993, 34 (34) : 5459 - 5462
[3] A new procedure for the isomerisation of substituted and unsubstituted allyl ethers of carbohydrates
Boons, GJ
Burton, A
Isles, S
[J]. CHEMICAL COMMUNICATIONS, 1996, (02) : 141 - 142
[4] CLEAVAGE OF ALLYL ETHERS WITH PD-C
BOSS, R
SCHEFFOLD, R
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1976, 15 (09): : 558 - 559
[5] Homogeneous metathesis polymerization by well-defined group VI and group VIII transition-metal alkylidenes: Fundamentals and applications in the preparation of advanced materials
Buchmeiser, MR
[J]. CHEMICAL REVIEWS, 2000, 100 (04) : 1565 - 1604
[6] ISOMERIZATION OF ALLYL ETHERS TO VINYL ETHERS CATALYZED BY PALLADIUM ON CARBON
CARLESS, HAJ
HAYWOOD, DJ
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1980, (20) : 980 - 981
[7] SELECTIVE CLEAVAGE OF ALLYL ETHERS UNDER MILD CONDITIONS BY TRANSITION-METAL REAGENTS
COREY, EJ
SUGGS, JW
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (18) : 3224 - 3224
[8] CUNNINGHAM J, 1964, TETRAHEDRON LETT, P1191
[9] DIAZ RR, 1994, J ORG CHEM, V59, P7928
[10] ASYMMETRIC DOUBLE-BOND ISOMERIZATION OF 4,7-DIHYDRO-1,3-DIOXEPIN TO 4,5-DIHYDRO-1,3-DIOXEPIN
FRAUENRATH, H
PHILIPPS, T
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1986, 25 (03): : 274 - 274

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