Highly diastereo- and enantioselective organocatalytic addition of acetone to β-substituted α-ketoesters via dynamic kinetic resolution

被引：20
作者：
Yang, Jin [1 ]
Wang, Ting [1 ]
Ding, Zhenhua [1 ]
Shen, Zongxuan [1 ]
Zhang, Yawen [1 ]
机构：
[1] Soochow Univ, Coll Chem & Chem Engn, Key Lab Organ Synth Jiangsu Prov, Suzhou 215123, Peoples R China
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2009年 / 7卷 / 10期
关键词：
ASYMMETRIC ALDOL REACTIONS; ORGANIC-SYNTHESIS; METHYL KETONES; AMINO-ACID; PROLINE; CATALYSTS; PHOSPHONATES; DERIVATIVES; REDUCTION; ENZYMES;
D O I：
10.1039/b822127h
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
L-Proline catalyzes the aldol addition reaction of acetone to beta-substituted alpha-ketoesters with dynamic kinetic resolution, providing the desired adduct in good yield with excellent diastereoselectivity ( up to >99:1 dr) and enantioselectivity (up to 98% ee). The absolute configuration of the chiral adduct was assigned by single-crystal X-ray diffraction analysis. A tentative explanation of the stereochemical outcome is proposed.
引用
收藏
页码：2208 / 2213
页数：6
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