Improved procedure for the room temperature asymmetric phase-transfer mediated epoxidation of α,β-unsaturated ketones

被引：71

作者：

Lygo, B ^{[1
]}

To, DCM ^{[1
]}

机构：

[1] Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 07期

关键词：

D O I：

10.1016/S0040-4039(00)02208-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Studies into the factors affecting the rate of reaction in the enantioselective epoxidation of alpha,beta -unsaturated ketones utilising Cinchona alkaloid-derived quaternary ammonium phase-transfer catalysts are reported. This has led to the identification of improved conditions for the room temperature epoxidation process, which require only I mol% catalyst and lead to isolation of the epoxide products in high enantiomeric excess. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：1343 / 1346

页数：4

共 21 条

[1] Asymmetric epoxidation of α,β-unsaturated ketones under phase-transfer catalyzed conditions
Arai, S
Tsuge, H
Shioiri, T
[J]. TETRAHEDRON LETTERS, 1998, 39 (41) : 7563 - 7566
[2] Mechanism and conditions for highly enantioselective epoxidation of α,β-enones using charge-accelerated catalysis by a rigid quaternary ammonium salt
Corey, EJ
Zhang, FY
[J]. ORGANIC LETTERS, 1999, 1 (08) : 1287 - 1290
[3] Highly enantioselective phase transfer catalyzed alkylation of a 3-oxygenated propionic ester equivalent; applications and mechanism
Corey, EJ
Bo, YX
Busch-Petersen, J
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (49) : 13000 - 13001
[4] Highly enantioselective synthesis of cyclic and functionalized α-amino acids by means of a chiral phase transfer catalyst
Corey, EJ
Noe, MC
Xu, F
[J]. TETRAHEDRON LETTERS, 1998, 39 (30) : 5347 - 5350
[5] 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
[6] Enantioselective PTC:: Varying the cinchona alkaloid motive
Dehmlow, EV
Wagner, S
Müller, A
[J]. TETRAHEDRON, 1999, 55 (20) : 6335 - 6346
[7] ANODIC-OXIDATION OF BENZYL ALCOHOL TO BENZALDEHYDE IN THE PRESENCE OF BOTH REDOX MEDIATOR AND PHASE-TRANSFER CATALYST
DO, JS
CHOU, TC
[J]. JOURNAL OF APPLIED ELECTROCHEMISTRY, 1989, 19 (06) : 922 - 927
[8] Enantioselective synthesis of β-hydroxy-α-amino acid esters by aldol coupling using a chiral quaternary ammonium salt as catalyst
Horikawa, M
Busch-Petersen, J
Corey, EJ
[J]. TETRAHEDRON LETTERS, 1999, 40 (20) : 3843 - 3846
[9] Enantioselective synthesis of bis-α-amino acid esters via asymmetric phase-transfer catalysis.
Lygo, B
Crosby, J
Peterson, JA
[J]. TETRAHEDRON LETTERS, 1999, 40 (07) : 1385 - 1388
[10] A new class of asymmetric phase-transfer catalysts derived from Cinchona alkaloids - Application in the enantioselective synthesis of alpha-amino acids
Lygo, B
Wainwright, PG
[J]. TETRAHEDRON LETTERS, 1997, 38 (49) : 8595 - 8598

← 1 2 3 →