Catalytic asymmetric Pauson-Khand-type reactions of enynes with formaldehyde in aqueous media

被引：52

作者：

Fuji, K ^{[1
]}

Morimoto, T ^{[1
]}

Tsutsumi, K ^{[1
]}

Kakiuchi, K ^{[1
]}

机构：

[1] Nara Inst Sci & Technol, Grad Sch Mat Sci, Nara 6300192, Japan

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 50期

基金：

日本学术振兴会;

关键词：

Pauson-Khand; asymmetric catalysis; enynes; formaldehyde;

D O I：

10.1016/j.tetlet.2004.10.100

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first example of an aqueous, asymmetric, and CO gas-free Pauson-Khand-type reaction is described. Using formaldehyde as a commercially available substitute for carbon monoxide, combined use of a hydrophilic phosphine (TPPTS) and a hydrophobic, chiral phosphine (tolBINAP) enable the reaction to proceed smoothly in aqueous media, even in the absence of carbon monoxide, and stereoselectively. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：9163 / 9166

页数：4

共 20 条

[1] Aqueous catalytic Pauson-Khand-type reactions of enynes with formaldehyde: Transfer carbonylation involving an aqueous decarbonylation and a micellar carbonylation
Fuji, K
Morimoto, T
Tsutsumi, K
Kakiuchi, K
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (21) : 2409 - 2411
[2] Identification of an asymmetric Pauson-Khand precatalyst
Gibson, SE
Lewis, SE
Loch, JA
Steed, JW
Tozer, MJ
[J]. ORGANOMETALLICS, 2003, 22 (26) : 5382 - 5384
[3] The Pauson-Khand reaction: the catalytic age is here!
Gibson, SE
Stevenazzi, A
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (16) : 1800 - 1810
[4] An intramolecular titanium-catalyzed asymmetric Pauson-Khand type reaction
Hicks, FA
Buchwald, SL
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (30) : 7026 - 7033
[5] Highly enantioselective catalytic Pauson-Khand type formation of bicyclic cyclopentenones
Hicks, FA
Buchwald, SL
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (46) : 11688 - 11689
[6] Asymmetric catalytic Pauson-Khand reactions with chiral phosphine ligands: Dramatic effects of substituents in 1,6-enyne systems
Hiroi, K
Watanabe, T
Kawagishi, R
Abe, I
[J]. TETRAHEDRON LETTERS, 2000, 41 (06) : 891 - 895
[7] Desymmetrization of meso-dienyne by asymmetric Pauson-Khand type reaction catalysts
Jeong, N
Kim, DH
Choi, JH
[J]. CHEMICAL COMMUNICATIONS, 2004, (09) : 1134 - 1135
[8] Rhodium(I)-catalyzed asymmetric intramolecular Pauson-Khand-type reaction
Jeong, N
Sung, BK
Choi, YK
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (28) : 6771 - 6772
[9] Aqueous-phase, thermal Pauson-Khand reactions in the presence of surfactants
Krafft, ME
Wright, JA
Boñaga, LVR
[J]. TETRAHEDRON LETTERS, 2003, 44 (16) : 3417 - 3422
[10] CO-transfer carbonylation reactions. A catalytic Pauson-Khand-type reaction of enynes with aldehydes as a source of carbon monoxide
Morimoto, T
Fuji, K
Tsutsumi, K
Kakiuchi, K
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (15) : 3806 - 3807

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