Enantioselective catalytic synthesis of ethyl mandelate derivatives using Rh(I)-NHC catalysts and organoboron reagents

被引：15
|
作者：
Marques, Carolina S.
Burke, Anthony J. [1 ]
机构：
[1] Univ Evora, Dept Chem, P-7000 Evora, Portugal
来源：
TETRAHEDRON-ASYMMETRY | 2013年 / 24卷 / 11期
关键词：
GLYOXYLATE-ENE REACTION; OXIDATION/BENZILIC ESTER REARRANGEMENT; ALPHA-HYDROXYCARBOXYLIC ACIDS; ARYLBORONIC ACIDS; ALPHA; BETA-UNSATURATED KETONES; ADDITION-REACTIONS; RHODIUM COMPLEXES; HYDROXY ESTERS; BORONIC ACIDS; BORIC-ACID;
D O I：
10.1016/j.tetasy.2013.04.011
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
Herein we describe for the first time the enantioselective catalytic arylation of ethyl glyoxalate using phenylboron reagents and chiral rhodium(I)-NHC catalysts. (KOBu)-Bu-t was the base of choice, along with tert-amyl alcohol as the solvent. A novel chiral bis-imidazolium salt was synthesized and evaluated for the first time in this catalytic transformation. Although moderate enantioselectivities (up to 34% ee) were obtained for the phenylation reaction, despite the excellent yields, very low enantioselectivities were obtained using other arylboronic acids with a variety of chiral rhodium(I)-NHC catalysts. (C) 2013 Elsevier Ltd. All rights reserved.
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页码：628 / 632
页数：5
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