Synthesis of C3-symmetric tris(β-hydroxy amide) ligands and their Ti(IV) complex-catalyzed enantioselective alkynylation of aldehydes

被引：82

作者：

Fang, T ^{[1
]}

Du, DM ^{[1
]}

Lu, SF ^{[1
]}

Xu, JX ^{[1
]}

机构：

[1] Peking Univ, Key Lab Bioorgan Chem & Mol Engn, Minist Educ, Coll Chem & Mol Engn, Beijing 100871, Peoples R China

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 11期

关键词：

D O I：

10.1021/ol050047v

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of new chiral C-3-symmetric tris(beta-hydroxy amide) ligands have been synthesized via the reaction of 1,3,5-benzenetricarboxylic chloride and optically pure amino alcohols (up to 96% yield). The asymmetric catalytic alkynylation of aldehydes with these new C3-symmetric chiral tris(beta-hydroxy amide) ligands and Ti ((OPr)-Pr-/)4 Was investigated. Ligand 4c synthesized from (1R,2S)-(-)-2-amino-1,2-diphenylethanol is effective for the enantioselective alkynylation of various aldehydes, and high enantioselectivity was obtained with aromatic aldehydes and alpha,beta-unsaturated aldehyde (up to 92% ee).

引用

页码：2081 / 2084

页数：4

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