Self-disproportionation of enantiomers of isopropyl 3,3,3-(trifluoro)lactate via sublimation: Sublimation rates vs. enantiomeric composition

被引：55

作者：

Yasumoto, Manabu ^{[2
]}

Ueki, Hisanori ^{[3
]}

Ono, Taizo ^{[4
]}

Katagiri, Toshimasa ^{[5
]}

Soloshonok, Vadim A. ^{[1
,6
]}

机构：

[1] Natl Acad Sci Ukraine, Inst Bioorgan Chem & Petrochem, UA-02660 Kiev 94, Ukraine

[2] Cent Glass Co, Kawagoe, Saitama 3501151, Japan

[3] Natl Inst Mat Sci, Tsukuba, Ibaraki 3050044, Japan

[4] Natl Inst Adv Ind Sci & Technol, Moriyama Ku, Nagoya, Aichi 4638560, Japan

[5] Okayama Univ, Okayama 7008530, Japan

[6] Univ Oklahoma, Dept Chem & Biochem, Norman, OK 73019 USA

来源：

JOURNAL OF FLUORINE CHEMISTRY | 2010年 / 131卷 / 04期

关键词：

Self-disproportionation of enantiomers; Optical purifications; Sublimation; Kinetic vs. thermodynamic; Fluorine and compounds; Racemic vs. enantiomerically pure compounds; Green; Environmentally friendly processes; ASYMMETRIC ALDOL REACTIONS; ACHIRAL-PHASE CHROMATOGRAPHY; FLUORINATED BENZALDEHYDES; STATIONARY-PHASE; SILICA-GEL; ACID; CRYSTALLIZATION; TRANSAMINATION; HOMOCHIRALITY; AMPLIFICATION;

D O I：

10.1016/j.jfluchem.2009.11.026

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The presented results convincingly demonstrate that self-disproportionation of enantiomers via sublimation is substantially more complex phenomenon then was previously believed. We demonstrate that the racemic form of isopropyl 3,3,3-trifluoro-2-hydroxypropanoate (1) sublimed faster regardless of the starting enantiomeric composition of the enantiomerically enriched mixtures studied in the range from 20.8, 36.8, 58.7 to 79.4% ee. This preferential sublimation of the racemic form allowed for, the most possibly simple, preparation of optically pure samples of compound 1. In this work we also suggest some general experimental procedures, which may be easily used to facilitate the interpretation of the data collected in different laboratories. (C) 2009 Elsevier B.V. All rights reserved.

引用

页码：535 / 539

页数：5

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