Copper catalyzed tandem asymmetric conjugate addition-cyclization reaction in the presence of chiral phosphoramidite ligands

被引：35

作者：

Li, KY ^{[1
]}

Alexakis, A ^{[1
]}

机构：

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

来源：

TETRAHEDRON LETTERS | 2005年 / 46卷 / 46期

基金：

新加坡国家研究基金会;

关键词：

copper; tandem; conjugate addition; cyclization; chiral; phosphoramidite ligands;

D O I：

10.1016/j.tetlet.2005.09.065

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Copper-catalyzed intramolecular conjugate addition-cyclization in the presence of chiral phosphoramidite ligands was described. Cyclic products with multiple chiral centers were obtained with up to 93:7 diastereomeric ratio and 94% ee. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：8019 / 8022

页数：4

共 24 条

[1] Copper-catalyzed tandem conjugate addition-electrophilic trapping: Ketones, esters, and nitriles as terminal electrophiles [J].

Agapiou, K ;

Cauble, DF ;

Krische, MJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (14) :4528-4529

[2] Catalytic crossed Michael cycloisomerization of thioenoates:: Total synthesis of (±)-ricciocarpin A [J].

Agapiou, K ;

Krische, MJ .

ORGANIC LETTERS, 2003, 5 (10) :1737-1740

[3] Biphenol-based phosphoramidite ligands for the enantioselective copper-catalyzed conjugate addition of diethylzinc [J].

Alexakis, A ;

Polet, D ;

Rosset, S ;

March, S .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (17) :5660-5667

[4] Biphenol-based ligands for Cu-catalyzed asymmetric conjugate addition [J].

Alexakis, A ;

Polet, D ;

Benhaim, C ;

Rosset, S .

TETRAHEDRON-ASYMMETRY, 2004, 15 (14) :2199-2203

[5]

Alexakis A, 2000, EUR J ORG CHEM, V2000, P4011, DOI 10.1002/1099-0690(200012)2000:24<4011::AID-EJOC4011>3.0.CO

[6]

2-D

[7] 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

[8] Tandem enantioselective conjugate addition: Electrophile trapping reactions. application in the formation of syn or anti aldols [J].

Alexakis, A ;

Trevitt, GP ;

Bernardinelli, G .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (18) :4358-4359

[9]

Alexakis A, 2002, EUR J ORG CHEM, V2002, P3221

[10] Enantioselective copper-catalyzed conjugate addition of dialkyl zinc to nitro-olefins [J].

Alexakis, A ;

Benhaim, C .

ORGANIC LETTERS, 2000, 2 (17) :2579-2581

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