Enantioselective copper-catalysed 1,4-addition of diethylzinc to cyclohexenone using chiral diphosphite ligands

被引：55

作者：

Pàmies, O ^{[1
]}

Net, G ^{[1
]}

Ruiz, A ^{[1
]}

Claver, C ^{[1
]}

机构：

[1] Univ Rovira & Virgili, Dept Quim Fis & Inorgan, Tarragona 43005, Spain

来源：

TETRAHEDRON-ASYMMETRY | 1999年 / 10卷 / 10期

关键词：

D O I：

10.1016/S0957-4166(99)00197-4

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Bulky diphosphite ligands derived from ribo- and xylofuranose were tested in the copper asymmetric catalytic addition of diethylzinc to 2-cyclohexenone. The xylose derivatives provide enantiomeric excesses in the range of 22-53%. We also describe the preparation of the ribofuranose diphosphite ligands. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：2007 / 2014

页数：8

共 38 条

[1] ENANTIOSELECTIVE CONJUGATE ADDITION OF GRIGNARD-REAGENTS TO ENONES CATALYZED BY CHIRAL CUPRATE COMPLEXES [J].

AHN, KH ;

KLASSEN, RB ;

LIPPARD, SJ .

ORGANOMETALLICS, 1990, 9 (12) :3178-3181

[2] AN EASY AND FAST WAY TO DETERMINE THE ENANTIOMERIC PURITY OF SUBSTITUTED CYCLANONES [J].

ALEXAKIS, A ;

FRUTOS, JC ;

MANGENEY, P .

TETRAHEDRON-ASYMMETRY, 1993, 4 (12) :2431-2434

[3] Asymmetric conjugate addition of diethyl zinc to enones with tartrate chiral phosphite ligands [J].

Alexakis, A ;

Vastra, J ;

Burton, J ;

Mangeney, P .

TETRAHEDRON-ASYMMETRY, 1997, 8 (19) :3193-3196

[4] Asymmetric conjugate addition of diethyl zinc to enones with chiral phosphorus ligands derived from TADDOL [J].

Alexakis, A ;

Vastra, J ;

Burton, J ;

Benhaim, C ;

Mangeney, P .

TETRAHEDRON LETTERS, 1998, 39 (43) :7869-7872

[5] CHIRAL PHOSPHORUS LIGANDS FOR THE ASYMMETRIC CONJUGATE ADDITION OF ORGANOCOPPER REAGENTS [J].

ALEXAKIS, A ;

FRUTOS, J ;

MANGENEY, P .

TETRAHEDRON-ASYMMETRY, 1993, 4 (12) :2427-2430

[6] NEW CHIRAL LIGAND FOR THE ASYMMETRIC CONJUGATE ADDITION OF ORGANOCOPPER REAGENTS TO ENONES [J].

ALEXAKIS, A ;

MUTTI, S ;

NORMANT, JF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (16) :6332-6334

[7] Asymmetric conjugate addition of diethyl zinc to enones with chiral phosphine ligands [J].

Alexakis, A ;

Burton, J ;

Vastra, J ;

Mangeney, P .

TETRAHEDRON-ASYMMETRY, 1997, 8 (24) :3987-3990

[8]

[Anonymous], ORGANOCOPPER REAGENT

[9] Copper-catalysed asymmetric conjugate addition of organometallic reagents to linear enones using thiourethane ligands [J].

Bennett, SMW ;

Brown, SM ;

Muxworthy, JP ;

Woodward, S .

TETRAHEDRON LETTERS, 1999, 40 (09) :1767-1770

[10] RHODIUM-CATALYZED ASYMMETRIC HYDROFORMYLATION WITH DIPHOSPHITE LIGANDS BASED ON SUGAR BACKBONES [J].

BUISMAN, GJH ;

MARTIN, ME ;

VOS, EJ ;

KLOOTWIJK, A ;

KAMER, PCJ ;

VANLEEUWEN, PWNM .

TETRAHEDRON-ASYMMETRY, 1995, 6 (03) :719-738

← 1 2 3 4 →