Enantioselective olefin epoxidation using homologous amine and iminium catalysts -: a direct comparison

被引：25

作者：

Goncalves, Maria-Helena

Martinez, Alexandre

Grass, Stephane

Bulman Page, Philip C.

Lacour, Jerome

机构：

[1] Univ Geneva, Dept Chim Organ, CH-1211 Geneva 4, Switzerland

[2] Univ Loughborough, Dept Chem, Loughborough LE11 3TU, Leics, England

来源：

TETRAHEDRON LETTERS | 2006年 / 47卷 / 30期

关键词：

D O I：

10.1016/j.tetlet.2006.05.132

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Homologous biphenyl and (diastereomeric) binaphthyl tertiary azepines and quaternary iminium salts were prepared from (+)-(S,S)-L-acetonamine. Both the amines and iminium ions behave as effective catalysts for the enantioselective epoxidation of unfunctionalized olefins (ee up to 83%). (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：5297 / 5301

页数：5

共 34 条

[1] Synthetic applications of nonmetal catalysts for homogeneous oxidations
Adam, W
Saha-Möller, CR
Ganeshpure, PA
[J]. CHEMICAL REVIEWS, 2001, 101 (11) : 3499 - 3548
[2] Adam W., 2004, ORG REACTIONS, V61, P219, DOI DOI 10.1039/C3SC52649F
[3] Epoxidation of alkenes by amine catalyst precursors: Implication of aminium ion and radical cation intermediates (vol 122, pg 8317, 2000)
Adamo, MFA
Aggarwal, VK
Sage, MA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (37) : 11223 - 11223
[4] Epoxidation of alkenes by amine catalyst precursors: Implication of aminium ion and radical cation intermediates
Adamo, MFA
Aggarwal, VK
Sage, MA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (34) : 8317 - 8318
[5] Highly regioselective and diastereoselective epoxidation of allylic amines with Oxone
Aggarwal, VK
Fang, GY
[J]. CHEMICAL COMMUNICATIONS, 2005, (27) : 3448 - 3450
[6] New insights in the mechanism of amine catalyzed epoxidation: Dual role of protonated ammonium salts as both phase transfer catalysts and activators of Oxone
Aggarwal, VK
Lopin, C
Sandrinelli, F
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (25) : 7596 - 7601
[7] Catalytic asymmetric synthesis of epoxides mediated by chiral iminium salts
Aggarwal, VK
Wang, MF
[J]. CHEMICAL COMMUNICATIONS, 1996, (02) : 191 - 192
[8] 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
[9] Exocyclic iminium salts as catalysts for alkene epoxidation by Oxone®
Armstrong, A
Ahmed, G
Garnett, I
Goacolou, K
Wailes, JS
[J]. TETRAHEDRON, 1999, 55 (08) : 2341 - 2352
[10] BARBARO P, 2001, CHEMTRACTS, V14, P274

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