Axially chiral tridentate isoquinoline derived ligands for diethylzinc addition to aldehydes

被引：5

作者：

Sweetman, Brian A. ^{[1
]}

Guiry, Patrick J. ^{[1
]}

机构：

[1] Univ Coll Dublin, Sch Chem, Ctr Synth & Chem Biol, Dublin 4, Ireland

来源：

TETRAHEDRON | 2018年 / 74卷 / 38期

关键词：

Axial chirality; Tridentate ligand; Asymmetric catalysis; Isoquinoline; Chiral alcohol; ATROPISOMERIC PHOSPHINAMINE LIGAND; BIS(OXAZOLINE) LIGANDS; ENANTIOSELECTIVE ADDITION; ALDOL ADDITIONS; RESOLUTION; COMPLEXATION; QUINAZOLINE; RECOGNITION; ALLYLATION; CHLORIDE;

D O I：

10.1016/j.tet.2018.07.048

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis and resolution of new tridentate isoquinoline-derived ligands has been developed. The key steps in the synthetic sequence include successive, chemo-selective Suzuki-Miyaura cross-couplings of 1,3-dichloroisoquinoline with suitable arylboronic acids. The new ligands prepared in this manner were resolved either via molecular complexation with N-benzylcinchonidinium chloride as with 1-[3-(2-hydroxyphenyl)isoquinolin-1-yl]naphthalen-2-ol or via chromatographic separation of its epimeric camphorsulfonates as for 1,3-bis-(2-hydroxynaphthalen-1-yl)isoquinoline. 4-tert-Butyl-2-chloro-6-[1-(2-hydroxymethylnaphthalen-1-yl)isoquinolin-3-yliphenol was resolved by chiral semi-preparative HPLC. The application of these ligands in the diethylzinc addition to aldehydes was investigated. In certain cases, the desired secondary alcohols were obtained in high yield with excellent enantiomeric excess (ee > 99%) at low catalyst loading (1 mol%). (C) 2018 Elsevier Ltd. All rights reserved.

引用

页码：5567 / 5581

页数：15

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