A Highly Diastereoselective Synthesis of α-Hydroxy-β-amino Acid Derivatives via a Lewis Acid Catalyzed Three-Component Condensation Reaction

被引：24

作者：

Gassa, Federico ^{[1
]}

Contini, Alessandro ^{[1
]}

Fontana, Gabriele ^{[2
]}

Pellegrino, Sara ^{[1
]}

Gelmi, Maria Luisa ^{[1
]}

机构：

[1] Univ Milan, DISMAB, Sez Chim Organ A Marchesini, Fac Farm, I-20133 Milan, Italy

[2] Indena SPA, I-20141 Milan, Italy

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 75卷 / 21期

关键词：

DESYMMETRIZED GLYCOLIC ACID; MANNICH-TYPE REACTIONS; KETENE SILYL ACETALS; ASYMMETRIC-SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; DENSITY FUNCTIONALS; THERMOCHEMICAL KINETICS; BIOLOGICAL EVALUATION; BARRIER HEIGHTS; CHIRAL IMINES;

D O I：

10.1021/jo1011762

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A very efficient three-component synthesis of a series of syn alpha-hydroxy-beta-amino esters, obtained in high diastereoselection and yield, was realized starting from an aldehyde, benzylamine, and the ketene silyl acetals derived from Ley's lactones. The synthetic protocol was optimized and the above compounds were obtained without the isolation of intermediates. The origin of the observed diastereoselection was investigated through a computational model of the key reaction step.

引用

页码：7099 / 7106

页数：8

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