Ni(II)-catalyzed conia-ene reaction of 1,3-dicarbonyl compounds with alkynes

被引：97

作者：

Gao, Q ^{[1
]}

Zheng, BF ^{[1
]}

Li, JH ^{[1
]}

Yang, D ^{[1
]}

机构：

[1] Univ Hong Kong, Dept Chem, Hong Kong, Hong Kong, Peoples R China

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 11期

关键词：

D O I：

10.1021/ol050532q

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We have discovered a Ni(II)-catalyzed Conia-ene reaction of 1,3-dicarbonyl compounds with alkynes. In the presence of Ni(acac)(2) and Yb(OTf)(3), various acetylenic 1,3-dicarbonyl compounds underwent Conia-ene reaction to give mono- and bicyclic olefinic cyclopentanes. A mechanism involving the enol-yne-Ni complex formation is proposed and supported by deuterium-labeling experiments.

引用

页码：2185 / 2188

页数：4

共 42 条

[1] FORMATION OF CYCLOPENTANES FROM DELTA-ETHYLENE MALONATES BY CATALYSIS IN PALLADIUM(0) - STEREOCHEMISTRY AND MECHANISM
BALME, G
BOUYSSI, D
FAURE, R
GORE, J
VANHEMELRYCK, B
[J]. TETRAHEDRON, 1992, 48 (19) : 3891 - 3902
[2] BOAVENTURA MA, 1983, SYNTHESIS-STUTTGART, P801
[3] Intramolecular carbocupration reaction of unactivated alkynes bearing a stabilized nucleophile: Application to the synthesis of iridoid monoterpenes.
Bouyssi, D
Monteiro, N
Balme, G
[J]. TETRAHEDRON LETTERS, 1999, 40 (07) : 1297 - 1300
[4] TRIFLUOROMETHANESULFONATO COMPLEXES OF NICKEL AND COBALT
BYINGTON, AR
BULL, WE
[J]. INORGANICA CHIMICA ACTA, 1977, 21 (02) : 239 - 244
[5] Caine D., 1991, Comprehensive Organic Synthesis, V3, P1
[6] Construction of quaternary stereocenters: New perspectives through enantioselective Michael reactions
Christoffers, J
Baro, A
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (15) : 1688 - 1690
[7] Christoffers J, 2001, ANGEW CHEM INT EDIT, V40, P4591, DOI 10.1002/1521-3773(20011217)40:24<4591::AID-ANIE4591>3.0.CO
[8] 2-V
[9] CONIA JM, 1975, SYNTHESIS-STUTTGART, P1
[10] Corey EJ, 1998, ANGEW CHEM INT EDIT, V37, P388, DOI 10.1002/(SICI)1521-3773(19980302)37:4<388::AID-ANIE388>3.0.CO

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