Regiochemistry of molybdenum-catalyzed O-H insertions of vinylcarbenoids

被引：25

作者：

Davies, HML ^{[1
]}

Yokota, Y ^{[1
]}

机构：

[1] SUNY Buffalo, Dept Chem, Buffalo, NY 14260 USA

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 25期

基金：

美国国家科学基金会;

关键词：

carbenes and carbenoids; diazo compounds; O-H insertion; molybdenum; rhodium;

D O I：

10.1016/S0040-4039(00)00745-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Molybdenum-catalyzed decomposition of vinyldiazoacetates generates vinylcarbenoids that preferentially react with alcohols at the vinylogous position of the vinylcarbenoid rather than at the carbenoid site. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：4851 / 4854

页数：4

共 24 条

[1] A stereospecific access to allylic systems using rhodium(II)-vinyl carbenoid insertion into Si-H, O-H, and N-H bonds
Bulugahapitiya, P
Landais, Y
ParraRapado, L
Planchenault, D
Weber, V
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (06) : 1630 - 1641
[2] Solution studies of Ru-2(O(2)CR)(4)(n)+ complexes (n=0, 1; O(2)CR=octanoate, crotonate, dimethylacrylate, benzoate, p-toluate) and solid-state structures of Ru-2(O2C-p-tolyl)(4)(THF)(2), [Ru-2(O2C-p-tolyl)(4)(THF)(2)](+)[BF4](-), and Ru-2(O2C-p-tolyl)(4)(CH3CN)(2): Investigations of the axial ligation of the Ru-2 core
Chisholm, MH
Christou, G
Folting, K
Huffman, JC
James, CA
Samuels, JA
Wesemann, JL
Woodruff, WH
[J]. INORGANIC CHEMISTRY, 1996, 35 (12) : 3643 - 3658
[3] Cotton F.A., 1993, MULTIPLE BONDS METAL
[4] Davies H. M. L., 1997, ALDRICHIM ACTA, V30, P107
[5] TANDEM CYCLOPROPANATION COPE REARRANGEMENT - A GENERAL-METHOD FOR THE CONSTRUCTION OF 7-MEMBERED RINGS
DAVIES, HML
[J]. TETRAHEDRON, 1993, 49 (24) : 5203 - 5223
[6] Asymmetric synthesis of 2,3-dihydrofurans by reaction of rhodium-stabilized vinylcarbenoids with vinyl ethers
Davies, HML
Ahmed, G
Calvo, RL
Churchill, MR
Churchill, DG
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (08) : 2641 - 2645
[7] Davies HML, 1998, CURR ORG CHEM, V2, P463
[8] CARBENOID VERSUS VINYLOGOUS REACTIVITY IN RHODIUM(II)-STABILIZED VINYLCARBENOIDS
DAVIES, HML
HU, BH
SAIKALI, E
BRUZINSKI, PR
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (16) : 4535 - 4541
[9] ANOMALOUS REACTIVITY OF MONO SUBSTITUTED RHODIUM STABILIZED VINYLCARBENOIDS
DAVIES, HML
SAIKALI, E
CLARK, TJ
CHEE, EH
[J]. TETRAHEDRON LETTERS, 1990, 31 (44) : 6299 - 6302
[10] Davies HML, 1999, ADV CYCLOAD, V5, P119

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