Synthesis of a C1 symmetric BINOL-terpyridine ligand and highly enantioselective methyl propiolate addition to aromatic aldehydes

被引：25

作者：

Chen, Xi ^{[1
]}

Chen, Wei ^{[1
]}

Wang, Li ^{[1
]}

Yu, Xiao-Qi ^{[1
]}

Huang, De-Shun ^{[1
]}

Pu, Lin ^{[2
]}

机构：

[1] Sichuan Univ, Minist Educ, Dept Chem, Key Lab Green Chem & Technol, Chengdu 610064, Peoples R China

[2] Univ Virginia, Dept Chem, Charlottesville, VA 22904 USA

来源：

TETRAHEDRON | 2010年 / 66卷 / 11期

基金：

美国国家科学基金会;

关键词：

BIFUNCTIONAL ASYMMETRIC CATALYSIS; GAMMA-HYDROXY-ALPHA; BETA-ACETYLENIC ESTERS; ALIPHATIC-ALDEHYDES; ALKYNYLATION; COMPLEXES; KETONES; GENERATION; ACETYLIDES; CYANATION; ALCOHOL;

D O I：

10.1016/j.tet.2010.01.058

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel C-1 symmetric BINOL-terpyridine ligand (R)-5 is synthesized. This ligand in combination with ZnEt2 and Ti((OPr)-Pr-1)(4) is found to catalyze the highly enantioselective reaction (up to 98% ee) of methyl propiolate with a variety of aromatic aldehydes at 0 degrees C to give the synthetically useful gamma-hydroxy-alpha,beta-acetylenic esters. In comparison with the previously reported BINOL system, the use of (R)-5 requires a reduced amount of the chiral ligand without the addition of a Lewis base. It shows higher enantioselectivity for a number of substrates. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：1990 / 1993

页数：4

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