Amino-sugar modular ligands-useful cores for the formation of asymmetric copper 1,4-addition catalysts

被引：22

作者：

De Roma, Antonella ^{[2
]}

Ruffo, Francesco ^{[2
]}

Woodward, Simon ^{[1
]}

机构：

[1] Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England

[2] Univ Naples Federico II, Dipartimento Chim Paolo Corradini, I-80126 Naples, Italy

来源：

CHEMICAL COMMUNICATIONS | 2008年 / 42期

基金：

英国工程与自然科学研究理事会;

关键词：

D O I：

10.1039/b813137f

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Modular phosphine ligands, synthesised rapidly from commercial N-acetylglucosamine, are very effective in copper(I)-catalysed 1,4-additions of ZnR2 to linear aliphatic enones (87-95% ee).

引用

页码：5384 / 5386

页数：3

共 37 条

[1]

Ahlbrecht H, 1998, EUR J ORG CHEM, V1998, P1371, DOI 10.1002/(SICI)1099-0690(199807)1998:7<1371::AID-EJOC1371>3.0.CO

[2]

2-K

[3] 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

[4] 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

[5] Acceleration of the conjugate addition of diethyl zinc to enones by either Cu(OTf)(2) or trivalent phosphorus ligands [J].

Alexakis, A ;

Vastra, J ;

Mangeney, P .

TETRAHEDRON LETTERS, 1997, 38 (44) :7745-7748

[6] Carbohydrates as building blocks of privileged ligands for multiphasic asymmetric catalysis [J].

Benessere, Vincenzo ;

De Roma, Antonella ;

Ruffo, Francesco .

CHEMSUSCHEM, 2008, 1 (05) :425-430

[7] Copper-catalysed asymmetric conjugate addition of organometallic reagents to linear enones [J].

Bennett, SMW ;

Brown, SM ;

Cunningham, A ;

Dennis, MR ;

Muxworthy, JP ;

Oakley, MA ;

Woodward, S .

TETRAHEDRON, 2000, 56 (18) :2847-2855

[8] 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

[9]

Börner C, 2001, EUR J ORG CHEM, V2001, P2435

[10] O,N,O′-tridentate ligands derived from carbohydrates in the V(IV)-promoted asymmetric oxidation of thioanisole [J].

Cucciolito, ME ;

Del Litto, R ;

Roviello, G ;

Ruffo, F .

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2005, 236 (1-2) :176-181

← 1 2 3 4 →