A new class of chiral tetrahydropyran-4-one catalyst for asymmetric epoxidation of alkenes

被引：15

作者：

Armstrong, A ^{[1
]}

Tsuchiya, T ^{[1
]}

机构：

[1] Univ London Imperial Coll Sci & Technol, Dept Chem, London SW7 2AZ, England

来源：

TETRAHEDRON | 2006年 / 62卷 / 2-3期

关键词：

epoxidation; asymmetric; ketone; dioxirane;

D O I：

10.1016/j.tet.2005.08.112

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new class of chiral alpha-oxygenated-tetrahydropyran-4-ones for asymmetric epoxidation of alkenes using Oxone (R) is described, affording epoxides with up to 83% ee. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：257 / 263

页数：7

共 44 条

[1] Transition state stereoelectronics in alkene epoxidations by fluorinated dioxiranes
Armstrong, A
Washington, I
Houk, KN
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (26) : 6297 - 6298
[2] Amine-catalyzed epoxidation of alkenes: A new mechanism for the activation of oxone
Armstrong, A
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (12) : 1460 - 1462
[3] Enantioselective epoxidation of alkenes catalyzed by 2-fluoro-N-carbethoxytropinone and related tropinone derivatives
Armstrong, A
Ahmed, G
Dominguez-Fernandez, B
Hayter, BR
Wailes, JS
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (24) : 8610 - 8617
[4] Asymmetric epoxidation catalyzed by esters of α-hydroxy-8-oxabicyclo[3.2.1]octan-3-one
Armstrong, A
Moss, WO
Reeves, JR
[J]. TETRAHEDRON-ASYMMETRY, 2001, 12 (20) : 2779 - 2781
[5] Catalytic enantioselective epoxidation of alkenes with a tropinone-derived chiral ketone
Armstrong, A
Hayter, BR
[J]. CHEMICAL COMMUNICATIONS, 1998, (05) : 621 - 622
[6] Alkene epoxidation catalyzed by bicyclo[3.2.1]octan-3-ones: effects of structural modifications on catalyst efficiency and epoxidation enantioselectivity
Armstrong, A
Hayter, BR
Moss, WO
Reeves, JR
Wailes, JS
[J]. TETRAHEDRON-ASYMMETRY, 2000, 11 (10) : 2057 - 2061
[7] First highly enantioselective epoxidation of alkenes with aldehyde/Oxone®
Bez, G
Zhao, CG
[J]. TETRAHEDRON LETTERS, 2003, 44 (40) : 7403 - 7406
[8] Improved enantioselectivity in the epoxidation of cinnamic acid derivatives with dioxiranes from keto bile acids
Bortolini, O
Fantin, G
Fogagnolo, M
Forlani, R
Maietti, S
Pedrini, P
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (16) : 5802 - 5806
[9] Chiral fluoro ketones for catalytic asymmetric epoxidation of alkenes with oxone
Denmark, SE
Matsuhashi, H
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (10) : 3479 - 3486
[10] Frohn M, 2000, SYNTHESIS-STUTTGART, P1979

← 1 2 3 4 5 →