Enantioselective copper-catalyzed conjugate addition of diethylzinc to enones using new chiral P,N ligands composed of (S)-2-alkyl-2-aminoethylphosphines and α-substituted pyridines

被引：47

作者：

Morimoto, T ^{[1
]}

Yamaguchi, Y ^{[1
]}

Suzuki, M ^{[1
]}

Saitoh, A ^{[1
]}

机构：

[1] Univ Shizuoka, Sch Pharmaceut Sci, Shizuoka 4228526, Japan

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 51期

关键词：

copper catalysts; chiral ligands; asymmetric conjugate addition; enones;

D O I：

10.1016/S0040-4039(00)01789-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

New P,N ligands prepared from (S)-2-alkyl-2-aminoethylphosphines and alpha -substituted pyridines are efficient chiral ligands for the copper-catalyzed conjugate addition of diethylzinc to 2-cyclohexen-1-one and chalcone. The best result (90-91% ee) for the cyclohexenone was obtained with Cu(OTf)(2) (0.7-1 mol%) and a P,N ligand 4 derived from (S)-1-(diphenylphosphino)-3-methyl-2-butanamine and 6-methylpyridine-2-carboxaldehyde. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：10025 / 10029

页数：5

共 38 条

[1] Alexakis A, 1999, SYNLETT, P1811
[2] CHIRAL PHOSPHORUS LIGANDS FOR THE ASYMMETRIC CONJUGATE ADDITION OF ORGANOCOPPER REAGENTS
ALEXAKIS, A
FRUTOS, J
MANGENEY, P
[J]. TETRAHEDRON-ASYMMETRY, 1993, 4 (12) : 2427 - 2430
[3] Copper-catalysed asymmetric conjugate addition of organometallic reagents to linear enones using thiourethane ligands
Bennett, SMW
Brown, SM
Muxworthy, JP
Woodward, S
[J]. TETRAHEDRON LETTERS, 1999, 40 (09) : 1767 - 1770
[4] CATALYTIC ENANTIOSELECTIVE CONJUGATE ADDITION OF DIALKYLZINC COMPOUNDS TO CHALCONES
BOLM, C
EWALD, M
FELDER, M
[J]. CHEMISCHE BERICHTE-RECUEIL, 1992, 125 (05): : 1205 - 1215
[5] Chataigner I, 2000, ANGEW CHEM INT EDIT, V39, P916, DOI 10.1002/(SICI)1521-3773(20000303)39:5<916::AID-ANIE916>3.0.CO
[6] 2-M
[7] ENANTIOSELECTIVE CONJUGATE ADDITION OF DIETHYLZINC TO CHALCONES CATALYZED BY CHIRAL NI(II) AMINOALCOHOL COMPLEXES
DEVRIES, AHM
JANSEN, JFGA
FERINGA, BL
[J]. TETRAHEDRON, 1994, 50 (15) : 4479 - 4491
[8] Diastereoselective synthesis of pyridyl substituted thiazolidin-4-ones. New ligands for the Cu(I) catalyzed asymmetric conjugate addition of diethylzinc to enones
deVries, AHM
Hof, RP
Staal, D
Kellogg, RM
Feringa, BL
[J]. TETRAHEDRON-ASYMMETRY, 1997, 8 (10) : 1539 - 1543
[9] DEVRIES AHM, 1996, ANGEW CHEM INT EDIT, V35, P23754
[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 4 →