Diphenylphosphinooxazoline ligands with a chiral binaphthyl backbone for Pd-catalyzed allylic alkylation

被引：113

作者：

Imai, Y ^{[1
]}

Zhang, WB ^{[1
]}

Kida, T ^{[1
]}

Nakatsuji, Y ^{[1
]}

Ikeda, I ^{[1
]}

机构：

[1] Osaka Univ, Fac Engn, Dept Appl Chem, Suita, Osaka 565, Japan

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 24期

关键词：

D O I：

10.1016/S0040-4039(98)00768-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Novel diphenylphosphinooxazoline ligands with a chiral binaphthyl backbone were prepared. It was interestingly found that the two diastereomeric ligands afforded two enantiomeric products, respectively, with excellent catalytic activities and enantioselectivities for the palladium-catalyzed allylic alkylation, regardless of the identical (S)-oxazoline ring existing in both ligands. This is the first example using an (S)-oxazoline ligand to afford an (R)-product for this reaction. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：4343 / 4346

页数：4

共 29 条

[21] New chiral ligands for the asymmetric copper catalyzed conjugate addition of Grignard reagents to enones
Stangeland, EL
Sammakia, T
[J]. TETRAHEDRON, 1997, 53 (48) : 16503 - 16510
[22] NITROGEN DONORS IN ORGANOMETALLIC CHEMISTRY AND HOMOGENEOUS CATALYSIS
TOGNI, A
VENANZI, LM
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1994, 33 (05): : 497 - 526
[23] Asymmetric transition metal-catalyzed allylic alkylations
Trost, BM
VanVranken, DL
[J]. CHEMICAL REVIEWS, 1996, 96 (01) : 395 - 422
[24] Catalytic asymmetric Wacker-type cyclization
Uozumi, Y
Kato, K
Hayashi, T
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (21) : 5063 - 5064
[25] Homochiral 2,2'-bis(oxazolyl)-1,1'-binaphthyls as ligands for copper(I)-catalyzed asymmetric cyclopropanation
Uozumi, Y
Kyota, H
Kishi, E
Kitayama, K
Hayashi, T
[J]. TETRAHEDRON-ASYMMETRY, 1996, 7 (06) : 1603 - 1606
[26] PREPARATION OF OPTICALLY-ACTIVE BINAPHTHYLMONOPHOSPHINES (MOPS) CONTAINING VARIOUS FUNCTIONAL-GROUPS
UOZUMI, Y
SUZUKI, N
OGIWARA, A
HAYASHI, T
[J]. TETRAHEDRON, 1994, 50 (15) : 4293 - 4302
[27] Novel C-2-symmetric diphosphine ligand with only the planar chirality of ferrocene
Zhang, WB
Kida, T
Nakatsuji, Y
Ikeda, I
[J]. TETRAHEDRON LETTERS, 1996, 37 (44) : 7995 - 7998
[28] Highly diastereoselective ortho-lithiation of 1,1'-bis-(oxazolinyl)ferrocene directed to C-2-symmetric chiral ligands
Zhang, WB
Adachi, Y
Hirao, T
Ikeda, I
[J]. TETRAHEDRON-ASYMMETRY, 1996, 7 (02) : 451 - 460
[29] Interesting and effective P,N-chelation of tetrasubstituted ferrocene ligands for palladium-catalyzed asymmetric allylic substitution
Zhang, WB
Hirao, T
Ikeda, I
[J]. TETRAHEDRON LETTERS, 1996, 37 (26) : 4545 - 4548

← 1 2 3 →