Asymmetric phase-transfer mediated epoxidation of α,β-unsaturated ketones using catalysts derived from Cinchona alkaloids

被引：167

作者：

Lygo, B ^{[1
]}

Wainwright, PG ^{[1
]}

机构：

[1] Univ Salford, Dept Chem, Salford M5 4WT, Lancs, England

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 12期

关键词：

D O I：

10.1016/S0040-4039(97)10779-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The enantioselective epoxidation of alpha,beta-unsaturated ketones utilising Cinchona alkaloid-derived quaternary ammonium phase-transfer catalysts bearing an N-anthracenylmethyl function are presented, It has been found that the O-benzyl derivatives of these catalysts in conjunction with sodium hypochlorite give high stereocontrol and application of this process to the enantioselective synthesis of a range of trans-alpha,beta-epoxy ketones (e.e. 69-89%) is presented. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：1599 / 1602

页数：4

共 35 条

[1] ASYMMETRIC EPOXIDATION OF CYCLIC ENONES UNDER CHIRAL PHASE-TRANSFER CONDITIONS
BABA, N
ODA, J
KAWAGUCHI, M
[J]. AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1986, 50 (12): : 3113 - 3117
[2] BABA N, 1989, B I CHEM RES KYOTO U, V67, P121
[3] PLATINUM-CATALYZED OXIDATIONS WITH HYDROGEN-PEROXIDE - THE (ENANTIOSELECTIVE) EPOXIDATION OF ALPHA,BETA-UNSATURATED KETONES
BACCIN, C
GUSSO, A
PINNA, F
STRUKUL, G
[J]. ORGANOMETALLICS, 1995, 14 (03) : 1161 - 1167
[4] ASYMMETRIC EPOXIDATION OF ELECTRON-POOR OLEFINS .5. INFLUENCE ON STEREOSELECTIVITY OF THE STRUCTURE OF POLY-ALPHA-AMINOACIDS USED AS CATALYSTS
BANFI, S
COLONNA, S
MOLINARI, H
JULIA, S
GUIXER, J
[J]. TETRAHEDRON, 1984, 40 (24) : 5207 - 5211
[5] AN EFFICIENT ASYMMETRIC-SYNTHESIS OF SUBSTITUTED PHENYL GLYCIDIC ESTERS
BAURES, PW
EGGLESTON, DS
FLISAK, JR
GOMBATZ, K
LANTOS, I
MENDELSON, W
REMICH, JJ
[J]. TETRAHEDRON LETTERS, 1990, 31 (45) : 6501 - 6504
[6] Asymmetric epoxidation of enones employing polymeric alpha-amino acids in non-aqueous media
Bentley, PA
Bergeron, S
Cappi, MW
Hibbs, DE
Hursthouse, MB
Nugent, TC
Pulido, R
Roberts, SM
Wu, LE
[J]. CHEMICAL COMMUNICATIONS, 1997, (08) : 739 - 740
[7] THE 1ST ENANTIOSELECTIVE SYNTHESIS OF POLYOXYGENATED ALPHA-HYDROXYDIHYDROCHALCONES AND CIRCULAR DICHROIC ASSESSMENT OF THEIR ABSOLUTE-CONFIGURATION
BEZUIDENHOUDT, BCB
SWANEPOEL, A
AUGUSTYN, JAN
FERREIRA, D
[J]. TETRAHEDRON LETTERS, 1987, 28 (41) : 4857 - 4860
[8] Catalytic asymmetric epoxidation of alpha,beta-unsaturated ketones promoted by lanthanoid complexes
Bougauchi, M
Watanabe, S
Arai, T
Sasai, H
Shibasaki, M
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (09) : 2329 - 2330
[9] SYNTHETIC ENZYMES .4. HIGHLY ENANTIOSELECTIVE EPOXIDATION BY MEANS OF POLYAMINOACIDS IN A TRIPHASE SYSTEM - INFLUENCE OF STRUCTURAL VARIATIONS WITHIN THE CATALYSTS
COLONNA, S
MOLINARI, H
BANFI, S
JULIA, S
MASANA, J
ALVAREZ, A
[J]. TETRAHEDRON, 1983, 39 (09) : 1635 - 1641
[10] A rational approach to catalytic enantioselective enolate alkylation using a structurally rigidified and defined chiral quaternary ammonium salt under phase transfer conditions
Corey, EJ
Xu, F
Noe, MC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (50) : 12414 - 12415

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