New chiral phosphinoimidazolidine ligand in palladium-catalyzed asymmetric allylic substitution

被引：16

作者：

Jin, MJ ^{[1
]}

Kim, SH ^{[1
]}

Lee, SJ ^{[1
]}

Kim, YM ^{[1
]}

机构：

[1] Inha Univ, Sch Chem Sci & Engn, Inchon 402751, South Korea

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 41期

关键词：

asymmetric catalysis; allylic substitution; imidazolidine; ligand; Pd catalyst;

D O I：

10.1016/S0040-4039(02)01676-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Chiral phosphinoimidazolidine 3 was used as an excellent ligand in Pd-catalyzed asymmetric allylic alkylation of racemic 1,3-diphenyt-2-propenyl acetate 5 with dimethyl malonate. Outstanding enantioselectivity of up to 99% and remarkable catalytic activity were observed. The ligand was also found to be effective in the asymmetric allylic amination of 5 with benzylamine. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：7409 / 7411

页数：3

共 50 条

[1] New chiral phosphinooxazolidine ligands for palladium-catalyzed asymmetric allylic substitution
Jin, MJ
Jung, JA
Kim, SH
[J]. TETRAHEDRON LETTERS, 1999, 40 (28) : 5197 - 5198
[2] New chiral phosphinooxathiane ligands for palladium-catalyzed asymmetric allylic substitution reactions
Nakano, H
Okuyama, Y
Hongo, H
[J]. TETRAHEDRON LETTERS, 2000, 41 (23) : 4615 - 4618
[3] Chiral hydrazones as ligands in asymmetric catalysts: Palladium-catalyzed allylic substitution
Mino, T
Imiya, W
Yamashita, M
[J]. SYNLETT, 1997, (05) : 583 - &
[4] Palladium-catalyzed asymmetric allylic substitution reactions using new chiral phosphinooxathiane ligands
Nakano, H
Okuyama, Y
Yanagida, M
Hongo, H
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (02): : 620 - 625
[5] Application of sSPhos as a Chiral Ligand for Palladium-Catalyzed Asymmetric Allylic Alkylation
Docherty, Philip J.
Kadarauch, Max
Mistry, Nisha
Phipps, Robert J.
[J]. ORGANIC LETTERS, 2023, 26 (14) : 2862 - 2866
[6] Design of bifunctional chiral phenanthroline ligand with Lewis basic site for palladium-catalyzed asymmetric allylic substitution
Naganawa, Yuki
Abe, Hiroki
Nishiyama, Hisao
[J]. CHEMICAL COMMUNICATIONS, 2018, 54 (21) : 2674 - 2677
[7] Palladium-catalyzed asymmetric tandem allylic substitution using chiral 2-(phosphinophenyl)pyridine ligand
Ito, K
Imahayashi, Y
Kuroda, T
Eno, S
Saito, B
Katsuki, T
[J]. TETRAHEDRON LETTERS, 2004, 45 (39) : 7277 - 7281
[8] A NEW CLASS OF CHIRAL PHOSPHORUS CATALYST FOR ASYMMETRIC PALLADIUM-CATALYZED ALLYLIC SUBSTITUTION-REACTIONS
BRENCHLEY, G
MERIFIELD, E
WILLS, M
FEDOULOFF, M
[J]. TETRAHEDRON LETTERS, 1994, 35 (17) : 2791 - 2794
[9] Palladium-catalyzed asymmetric allylic substitution using planar chiral hydrazone ligands
Mino, T
Ogawa, T
Yamashita, M
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2003, 665 (1-2) : 122 - 126
[10] Chiral β-phosphino sulfoxides as chiral ligands in palladium-catalyzed asymmetric allylic nucleophilic substitution reactions
Hiroi, K
Suzuki, Y
Kawagishi, R
[J]. TETRAHEDRON LETTERS, 1999, 40 (04) : 715 - 718

← 1 2 3 4 5 →