Evans Enolates: Solution Structures of Lithiated Oxazolidinone-Derived Enolates

被引：25

作者：

Tallmadge, Evan H. ^{[1
]}

Collum, David B. ^{[1
]}

机构：

[1] Cornell Univ, Dept Chem & Chem Biol, Baker Lab, Ithaca, NY 14853 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2015年 / 137卷 / 40期

基金：

美国国家卫生研究院;

关键词：

RAY CRYSTAL-STRUCTURE; CHIRAL LITHIUM AMIDE; ASYMMETRIC-SYNTHESIS; ALDOL CONDENSATION; DEGENERATE TRANSESTERIFICATION; STEREOSELECTIVE-SYNTHESIS; ANIONIC-POLYMERIZATION; CONVENIENT METHOD; NMR-SPECTROSCOPY; WEAKLY POLAR;

D O I：

10.1021/jacs.5b08207

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The results of a combination of Li-6 and C-13 NMR spectroscopic and computational studies of oxazolidinone-based lithium enolates-Evans enolates-in tetrahydrofuran (THF) solution revealed a mixture of dimers, tetramers, and oligomers (possibly ladders). The distribution depended on the structure of the oxazolidinone auxiliary, substituent on the enolate, and THF concentration (in THF/toluene mixtures). The unsolvated tetrameric form contained a D-2d-symmetric core structure, whereas the dimers were determined experimentally and computationally to be trisolvates with several isomeric forms.

引用

页码：13087 / 13095

页数：9

共 127 条

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