Organocatalytic Enantioselective Synthesis of α-Hydroxyketones through a Friedel-Crafts Reaction of Naphthols and Activated Phenols with Aryl- and Alkylglyoxal Hydrates

被引：25
作者：
Vila, Carlos [1 ]
Quintero, Lucia [1 ]
Blay, Gonzalo [1 ]
Carmen Munoz, M. [2 ]
Pedro, Jose R. [1 ]
机构：
[1] Univ Valencia, Fac Quim, Dept Quim Organ, C Dr Moliner 50, E-46100 Valencia, Spain
[2] Univ Politecn Valencia, Dept Fis Aplicada, C Cami de Vera S-N, E-46022 Valencia, Spain
来源：
ORGANIC LETTERS | 2016年 / 18卷 / 21期
关键词：
DYNAMIC KINETIC RESOLUTION; INTRAMOLECULAR CANNIZZARO REACTION; ASYMMETRIC BENZOIN CONDENSATION; ELECTRON-RICH PHENOLS; ONE-POT SYNTHESIS; HIGHLY EFFICIENT; CINCHONA ALKALOIDS; CARBONYL-COMPOUNDS; (R)-ALPHA-HYDROXY KETONES; STEREOSELECTIVE-SYNTHESIS;
D O I：
10.1021/acs.orglett.6b02893
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient organocatalytic asymmetric synthesis of alpha-hydroxyketones has been developed. Quinine-derived thiourea catalyzed the enantioselective Friedel Crafts alkylation of naphthols and activated phenols with aryl- and alkylglyoxal hydrates, providing the corresponding chiral alpha-hydroxyketones with high yields (up to 97%) and excellent enantioselectivities (up to 99% ee).
引用
收藏
页码：5652 / 5655
页数：4
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