Chiral thiazoline ligands: application in Pd-catalysed allylic substitution

被引：63

作者：

Abrunhosa, I ^{[1
]}

Delain-Bioton, L ^{[1
]}

Gaumont, AC ^{[1
]}

Gulea, M ^{[1
]}

Masson, S ^{[1
]}

机构：

[1] ENSICAEN Univ, CNRS, UMR 6507, Lab Chim Mol & Thioorgan, F-14050 Caen, France

来源：

TETRAHEDRON | 2004年 / 60卷 / 41期

关键词：

thiazolines; oxazolines; chiral ligands; asymmetric catalysis; allylic substitution;

D O I：

10.1016/j.tet.2004.07.048

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of thiazoline ligands, analogues of well-known oxazolines, easily prepared from chiral aminoalcohols, and appropriate dithioesters, was tested in the Pd-catalysed allylic substitution. A systematic comparison with the corresponding oxazolines (using literature data or our own tests) has been made for each case. Some important differences (between their catalytic activity and enantioselectivity) were noted for the two types of ligands, especially in the case of bis(thiazolines) and bis(oxazolines). (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：9263 / 9272

页数：10

共 41 条

[31] Preparation of chiral phosphorus, sulfur and selenium containing 2-aryloxazolines [J].

Peer, M ;

deJong, JC ;

Kiefer, M ;

Langer, T ;

Rieck, H ;

Schell, H ;

Sennhenn, P ;

Sprinz, J ;

Steinhagen, H ;

Wiese, B ;

Helmchen, G .

TETRAHEDRON, 1996, 52 (21) :7547-7583

[32] Chiral heterocycles as ligands in asymmetric catalysis [J].

Pfaltz, A .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1999, 36 (06) :1437-1451

[33] Design of chiral ligands for asymmetric catalysis: From C-2-symmetric semicorrins and bisoxazolines to non-symmetric phosphinooxazolines [J].

Pfaltz, A .

ACTA CHEMICA SCANDINAVICA, 1996, 50 (03) :189-194

[34] CHIRAL SEMICORRINS AND RELATED NITROGEN-HETEROCYCLES AS LIGANDS IN ASYMMETRIC CATALYSIS [J].

PFALTZ, A .

ACCOUNTS OF CHEMICAL RESEARCH, 1993, 26 (06) :339-345

[35]

REISER O, 1993, ANGEW CHEM INT EDIT, V32, P547, DOI 10.1002/anie.199305471

[36] PHOSPHINOARYLOXAZOLINES AND PHOSPHINOALKYLOXAZOLINES AS NEW CHIRAL LIGANDS FOR ENANTIOSELECTIVE CATALYSIS - VERY HIGH ENANTIOSELECTIVITY IN PALLADIUM CATALYZED ALLYLIC SUBSTITUTIONS [J].

SPRINZ, J ;

HELMCHEN, G .

TETRAHEDRON LETTERS, 1993, 34 (11) :1769-1772

[37] Palladium-catalyzed allylic alkylation with phosphinoaryldihydrooxazole ligands: First evidence and NMR spectroscopic structure determination of a primary olefin-Pd-o complex [J].

Steinhagen, H ;

Reggelin, M ;

Helmchen, G .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (19) :2108-2110

[38] Asymmetric synthesis of ferrocenylazido alcohols and their derivatization to novel chiral ferrocenyl-thiazoline ligands with C2-symmetry [J].

Tárraga, A ;

Molina, P ;

Curiel, D ;

Bautista, D .

TETRAHEDRON-ASYMMETRY, 2002, 13 (15) :1621-1628

[39] Asymmetric transition metal-catalyzed allylic alkylations [J].

Trost, BM ;

VanVranken, DL .

CHEMICAL REVIEWS, 1996, 96 (01) :395-422

[40] CHIRAL PHOSPHINOARYLDIHYDROOXAZOLES AS LIGANDS IN ASYMMETRIC CATALYSIS - PD-CATALYZED ALLYLIC SUBSTITUTION [J].

VONMATT, P ;

PFALTZ, A .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1993, 32 (04) :566-568

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