Copper-catalyzed desymmetrization of oxabenzonorbornadienes with aluminum reagents

被引：54

作者：

Millet, Renaud ^{[1
]}

Bernardez, Tania ^{[1
]}

Palais, Laetitia ^{[1
]}

Alexakis, Alexandre ^{[1
]}

机构：

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

来源：

TETRAHEDRON LETTERS | 2009年 / 50卷 / 26期

基金：

新加坡国家研究基金会;

关键词：

ASYMMETRIC CONJUGATE ADDITION; RING-OPENING REACTIONS; OXABICYCLIC ALKENES; ALLYLIC ALKYLATION; HETEROBICYCLIC ALKENES; PHOSPHINE LIGAND; COMPLEXES; ENANTIOSELECTIVITY; BIDENTATE; AZA;

D O I：

10.1016/j.tetlet.2009.02.219

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The desymmetrization of oxabenzonorbornadienes with aluminum reagents and SimplePhos as chiral ligand is described. The corresponding homoallylic alcohols are obtained in high yield, diastereoselectivity, and enantiomeric excess. Furthermore the first anti enantioselective desymmetrization with aromatic nucleophiles is reported. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：3474 / 3477

页数：4

共 36 条

[1] Enantioselective copper-catalyzed conjugate addition and allylic substitution reactions [J].

Alexakis, A. ;

Backvall, J. E. ;

Krause, N. ;

Pamies, O. ;

Dieguez, M. .

CHEMICAL REVIEWS, 2008, 108 (08) :2796-2823

[2] 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

[3] Copper-catalyzed ring-opening of heterobicyclic alkenes with Grignard reagents:: Remarkably high anti-stereocontrol [J].

Arrayás, RG ;

Cabrera, S ;

Carretero, JC .

SYNTHESIS-STUTTGART, 2006, (07) :1205-1219

[4] Copper-catalyzed anti-stereocontrolled ring opening of oxabicyclic alkenes with Grignard reagents [J].

Arrayás, RG ;

Cabrera, S ;

Carretero, JC .

ORGANIC LETTERS, 2003, 5 (08) :1333-1336

[5] Copper phosphoramidite catalyzed enantioselective ring-opening of oxabicyclic alkenes: Remarkable reversal of stereocontrol [J].

Bertozzi, F ;

Pineschi, M ;

Macchia, F ;

Arnold, LA ;

Minnaard, AJ ;

Feringa, BL .

ORGANIC LETTERS, 2002, 4 (16) :2703-2705

[6] On the use of phosphoramidite ligands in copper-catalyzed asymmetric transformations with trialkylaluminum reagents [J].

Bournaud, Chloee ;

Falciola, Caroline ;

Lecourt, Thomas ;

Rosset, Stephane ;

Alexakis, Alexandre ;

Micouin, Laurent .

ORGANIC LETTERS, 2006, 8 (16) :3581-3584

[7] Cationic planar chiral palladium PS complexes as highly efficient catalysts in the enantioselective ring opening of oxa- and azabicyclic alkenes [J].

Cabrera, S ;

Arrayás, RG ;

Carretero, JC .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (30) :3944-3947

[8] Fesulphos-palladium(II) complexes as well-defined catalysts for enantioselective ring opening of meso heterobicyclic alkenes with organozinc reagents [J].

Cabrera, S ;

Arrayás, RG ;

Alonso, I ;

Carretero, JC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (50) :17938-17947

[9] 3,5-dialkyl effect on enantioselectivity in Pd chemistry: Applications involving both bidentate and monodentate auxiliaries [J].

Dotta, P ;

Kumar, PGA ;

Pregosin, PS ;

Albinati, A ;

Rizzato, S .

ORGANOMETALLICS, 2004, 23 (10) :2295-2304

[10] Catalytic asymmetric conjugate addition and allylic alkylation with Grignard reagents [J].

Harutyunyan, Syuzanna R. ;

den Hartog, Tim ;

Geurts, Koen ;

Minnaard, Adriaan J. ;

Feringa, Ben L. .

CHEMICAL REVIEWS, 2008, 108 (08) :2824-2852

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