Biphenol-based phosphoramidite ligands for the enantioselective copper-catalyzed conjugate addition of diethylzinc

被引：120

作者：

Alexakis, A ^{[1
]}

Polet, D ^{[1
]}

Rosset, S ^{[1
]}

March, S ^{[1
]}

机构：

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

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 69卷 / 17期

关键词：

D O I：

10.1021/jo049359m

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Phosphoramidite ligands, based on ortho-substituted biphenols and a chiral amine, induce high enantioselectivities (ee's up to 99%) in the copper-catalyzed conjugate addition of dialkylzinc reagents to a variety of Michael acceptors. Particularly, the best reported ee's were obtained for acyclic nitroolefins.

引用

页码：5660 / 5667

页数：8

共 28 条

[1] A practical, solvent free, one-pot synthesis of C2-symmetrical secondary amines [J].

Alexakis, A ;

Gille, S ;

Prian, F ;

Rosset, S ;

Ditrich, K .

TETRAHEDRON LETTERS, 2004, 45 (07) :1449-1451

[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]

Alexakis A, 2001, SYNLETT, P1375

[4]

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

[5]

[Anonymous], TRANSITION METAL CAT

[6]

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

[7] Chiral cooperativity in diastereomeric diphosphite ligands: Effects on the rhodium-catalyzed enantioselective hydroformylation of styrene [J].

Buisman, GJH ;

vanderVeen, LA ;

Klootwijk, A ;

deLange, WGJ ;

Kamer, PCJ ;

vanLeeuwen, PWNM ;

Vogt, D .

ORGANOMETALLICS, 1997, 16 (13) :2929-2939

[8] New imidazole-based tripodal ligands as CuB site mimics of cytochrome c oxidase [J].

Collman, JP ;

Zhong, M ;

Costanzo, S ;

Zhang, C .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (24) :8252-8256

[9] MASS-SPECTRA AND PYROLYSES OF ORTHO PHENYLENE SULFITE AND RELATED COMPOUNDS [J].

DEJONGH, DC ;

VANFOSSE.RY .

JOURNAL OF ORGANIC CHEMISTRY, 1972, 37 (08) :1129-&

[10] New chiral oxazoline-phosphite ligands for the enantioselective copper-catalyzed 1,4-addition of organozinc reagents to enones [J].

Escher, IH ;

Pfaltz, A .

TETRAHEDRON, 2000, 56 (18) :2879-2888

← 1 2 3 →