Synthesis, resolution and racemisation studies of new tridentate ligands for asymmetric catalysis

被引：97

作者：

Sweetman, BA ^{[1
]}

Müller-Bunz, H ^{[1
]}

Guiry, PJ ^{[1
]}

机构：

[1] Univ Coll Dublin, Dept Chem, Conway Inst Biomed & Biomol Res, Ctr Synth & Chem Biol, Dublin 4, Ireland

来源：

TETRAHEDRON LETTERS | 2005年 / 46卷 / 27期

关键词：

Atropisomerism; Biaryls; Racemisation; Resolution; Suzuki cross-coupling;

D O I：

10.1016/j.tetlet.2005.04.139

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A method for the high-yielding preparation of two tridentate, isoquinoline-derived ligands, involving successive Suzuki cross-coupling reactions, is described. The first ligand Could be resolved via molecular complexation with N-benzylcinchonidinium chloride, while the second was resolved by chromatographic separation of its epimeric carnphorsulfonates. The barrier to rotation about the central biaryl axis was evaluated via racemisation Studies, and the absolute configuration assigned by X-ray crystallography. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：4643 / 4646

页数：4

共 18 条

[1]

[Anonymous], 1993, HDB ENANTIOSELECTIVE

[2]

Cagle F. W., 1951, J. Am. Chem. Soc., V73, P5628

[3] CATALYTIC, ENANTIOSELECTIVE ALDOL ADDITIONS WITH METHYL AND ETHYL-ACETATE O-SILYL ENOLATES - A CHIRAL TRIDENTATE CHELATE AS A LIGAND FOR TITANIUM(IV) [J].