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
Alexakis, A
Gille, S
Prian, F
Rosset, S
Ditrich, K
[J]. TETRAHEDRON LETTERS, 2004, 45 (07) : 1449 - 1451
[2] Dramatic improvement of the enantiomeric excess in the asymmetric conjugate addition reaction using new experimental conditions
Alexakis, A
Benhaim, C
Rosse, S
Humam, M
[J]. 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
Buisman, GJH
vanderVeen, LA
Klootwijk, A
deLange, WGJ
Kamer, PCJ
vanLeeuwen, PWNM
Vogt, D
[J]. ORGANOMETALLICS, 1997, 16 (13) : 2929 - 2939
[8] New imidazole-based tripodal ligands as CuB site mimics of cytochrome c oxidase
Collman, JP
Zhong, M
Costanzo, S
Zhang, C
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (24) : 8252 - 8256
[9] MASS-SPECTRA AND PYROLYSES OF ORTHO PHENYLENE SULFITE AND RELATED COMPOUNDS
DEJONGH, DC
VANFOSSE.RY
[J]. 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
Escher, IH
Pfaltz, A
[J]. TETRAHEDRON, 2000, 56 (18) : 2879 - 2888

← 1 2 3 →