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.

引用

页码：628 / 632

页数：5

共 48 条

[1] Asymmetric catalytic arylation of ethyl glyoxylate using organoboron reagents and Rh(I)-phosphane and phosphane-phosphite catalysts
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[2] Chiral Diphosphane- and NHC-Containing Ruthenium Catalysts for the Catalytic Asymmetric Arylation of Aldimines with Organoboron Reagents
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