Enantioselective opening of cyclic vinyl epoxides with organoaluminium reagents catalysed by copper salts

被引：23

作者：

Equey, O ^{[1
]}

Alexakis, A ^{[1
]}

机构：

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

来源：

TETRAHEDRON-ASYMMETRY | 2004年 / 15卷 / 10期

关键词：

D O I：

10.1016/j.tetasy.2004.04.011

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Herein we report conditions for the enantioselective conjugate addition of trialkylaluminium reagents to cyclic vinyl epoxides catalysed by copper salts and chiral phosphorus-based ligands. The reaction must be carried out in THE, otherwise we observed only oligomeric products. The best ees have been obtained with CuTC as the copper salt and a 2,2'-binaphthyl-based phosphorus ligand. Both opening products (S(N)2 and S(N)2' pathways) were obtained with good enantioselectivity and moderate to good regioselectivity. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：1531 / 1536

页数：6

共 18 条

[1] Dramatic improvement of the enantiomeric excess in the asymmetric conjugate addition reaction using new experimental conditions [J].

Alexakis, A ;

Benhaim, C ;

Rosse, S ;

Humam, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (19) :5262-5263

[2]

Alexakis A, 2001, SYNLETT, P1375

[3] Catalytic enantioselective carbon-carbon bond formation by addition of dialkylzinc reagents to cyclic 1,3-diene monoepoxides. [J].

Badalassi, F ;

Crotti, P ;

Macchia, F ;

Pineschi, M ;

Arnold, A ;

Feringa, BL .

TETRAHEDRON LETTERS, 1998, 39 (42) :7795-7798

[4] A new diastereo- and enantioselective copper-catalyzed conversion of alkynyl epoxides into α-allenic alcohols. [J].

Bertozzi, F ;

Crotti, P ;

Macchia, F ;

Pineschi, M ;

Arnold, A ;

Feringa, BL .

TETRAHEDRON LETTERS, 1999, 40 (26) :4893-4896

[5] A new catalytic and enantioselective desymmetrization of symmetrical methylidene cycloalkene oxides [J].

Bertozzi, F ;

Crotti, P ;

Macchia, F ;

Pineschi, M ;

Arnold, A ;

Feringa, BL .

ORGANIC LETTERS, 2000, 2 (07) :933-936

[6]

Bertozzi F, 2001, SYNTHESIS-STUTTGART, P483

[7]

Bertozzi F, 2001, ANGEW CHEM INT EDIT, V40, P930, DOI 10.1002/1521-3773(20010302)40:5<930::AID-ANIE930>3.0.CO

[8]

2-7

[9]

Breit B, 2002, MODERN ORGANOCOPPER CHEMISTRY, P188, DOI 10.1002/3527600086.ch6

[10] Catalytic enantioselective desymmetrization of COT-monoepoxide.: Maximum deviation from coplanarity for an SN2′-cuprate alkylation [J].

Del Moro, F ;

Crotti, P ;

Di Bussolo, V ;

Macchia, F ;

Pineschi, M .

ORGANIC LETTERS, 2003, 5 (11) :1971-1974

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