Asymmetric allylic substitution reaction with nitrogen and oxygen nucleophiles using monodentate chiral phosphine, 9-PBN

被引：42

作者：

Hamada, Y

Seto, N

Takayanagi, Y

Nakano, T

Hara, O

机构：

[1] Chiba Univ, Fac Pharmaceut Sci, Inage Ku, Chiba 2638522, Japan

[2] Nagoya City Univ, Fac Pharmaceut Sci, Mizuho Ku, Nagoya, Aichi 4678603, Japan

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 44期

关键词：

allylation; phosphines; palladium and compounds; asymmetric synthesis;

D O I：

10.1016/S0040-4039(99)01617-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Asymmetric allylic substitution reactions between 1,3-diphenyl-2-propenyl acetate and various hetero nucleophiles were efficiently carried out using the catalysts derived from the monodentate phosphine ligands, (1R, 2S, 5R, 6S)-2,6-dimethyl-9-phenyl-9-phosphabicyc[3.3.1]nonane and its enantiomer ((-)- and (+)-9-PBNs), and palladium (0). (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：7791 / 7794

页数：4

共 43 条

[1] Syntheses of novel chiral monophosphines, 2,5-dialkyl-7-phenyl-7-phosphabicyclo[2.2.1]heptanes, and their application in highly enantioselective Pd-catalyzed allylic alkylations
Chen, ZG
Jiang, QZ
Zhu, GX
Xiao, DM
Cao, P
Guo, C
Zhang, XM
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (13) : 4521 - 4523
[2] ENANTIOSELECTIVE HOMOGENEOUS CATALYSIS INVOLVING TRANSITION-METAL ALLYL INTERMEDIATES
CONSIGLIO, G
WAYMOUTH, RM
[J]. CHEMICAL REVIEWS, 1989, 89 (01) : 257 - 276
[3] Constantieux T, 1998, SYNLETT, P49
[4] PALLADIUM-CATALYZED ALLYLIC SUBSTITUTION-REACTIONS OF PROCHIRAL AND RACEMIC ALLYL ACETATES
DAWSON, GJ
WILLIAMS, JMJ
COOTE, SJ
[J]. TETRAHEDRON LETTERS, 1995, 36 (03) : 461 - 462
[5] ASYMMETRIC PALLADIUM-CATALYZED ALLYLIC SUBSTITUTION USING PHOSPHORUS-CONTAINING OXAZOLINE LIGANDS
DAWSON, GJ
FROST, CG
WILLIAMS, JMJ
[J]. TETRAHEDRON LETTERS, 1993, 34 (19) : 3149 - 3150
[6] ENANTIOSELECTIVE PALLADIUM CATALYZED ALLYLIC SUBSTITUTION WITH THIENYL OXAZOLINE LIGANDS
FROST, CG
WILLIAMS, JMJ
[J]. TETRAHEDRON LETTERS, 1993, 34 (12) : 2015 - 2018
[7] SELECTIVITY IN PALLADIUM CATALYZED ALLYLIC SUBSTITUTION
FROST, CG
HOWARTH, J
WILLIAMS, JMJ
[J]. TETRAHEDRON-ASYMMETRY, 1992, 3 (09) : 1089 - 1122
[8] Pd-catalyzed asymmetric synthesis of allylic tert-butyl sulfones and sulfides:: Kinetic resolution of the allylic substrate by a chiral Pd-complex
Gais, HJ
Eichelmann, H
Spalthoff, N
Gerhards, F
Frank, M
Raabe, G
[J]. TETRAHEDRON-ASYMMETRY, 1998, 9 (02) : 235 - 248
[9] New monodentate chiral phosphine 2,6-dimethyl-9-phenyl-9-phosphabicyclo[3.3.1]nonane(9-PBN): Application to asymmetric allylic substitution reaction
Hamada, Y
Seto, N
Ohmori, H
Hatano, K
[J]. TETRAHEDRON LETTERS, 1996, 37 (42) : 7565 - 7568
[10] ASYMMETRIC-SYNTHESIS CATALYZED BY CHIRAL FERROCENYLPHOSPHINE TRANSITION-METAL COMPLEXES .8. PALLADIUM-CATALYZED ASYMMETRIC ALLYLIC AMINATION
HAYASHI, T
YAMAMOTO, A
ITO, Y
NISHIOKA, E
MIURA, H
YANAGI, K
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (16) : 6301 - 6311

← 1 2 3 4 5 →