Structural and electronic effects of oxazolidine ligands derived from (1R,2S)-ephedrine in the asymmetric addition of diethylzinc to aldehydes

被引：11

作者：

Blocka, Ewelina ^{[1
]}

Jaworska, Magdalena ^{[1
]}

Kozakiewicz, Anna ^{[2
]}

Welniak, Miroslaw ^{[1
]}

Wojtczak, Andrzej ^{[2
]}

机构：

[1] Nicholas Copernicus Univ, Dept Organ Chem, PL-87100 Torun, Poland

[2] Nicholas Copernicus Univ, Dept Crystallochem & Biocrystallog, PL-87100 Torun, Poland

来源：

TETRAHEDRON-ASYMMETRY | 2010年 / 21卷 / 05期

关键词：

ENANTIOSELECTIVE ADDITION; ORGANOZINC REAGENTS; CATALYSTS; SALICYLALDEHYDE; HYDROXY; AMIDE;

D O I：

10.1016/j.tetasy.2010.02.029

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The purpose of this research was to determine the activity of chiral oxazolidine ligands prepared from (1R,2S)-ephedrine for the enantioselective addition of diethylzinc to aldehydes. The configuration on the newly formed C2 stereogenic center was determined as (2S) by X-ray structural analysis. Oxazolidine ligands reveal medium enantioselectivity with the ee exceeding 57%, and the yields obtained being 68-99%. The results indicate that the absolute configuration of the addition product depends not only on the N3-methyl as an important stereocontrol element but also on both the electronic and steric effects of the substrates and oxazolidine ligands. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：571 / 577

页数：7

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