ENANTIOMERIC ENRICHMENT OF SULFOXIDES BY PREPARATIVE FLASH CHROMATOGRAPHY ON AN ACHIRAL PHASE

被引：117

作者：

DITER, P

TAUDIEN, S

SAMUEL, O

KAGAN, HB

机构：

[1] Laboratoire de Synthése Asymétrique, URA CNRS 1497, Institut de Chimie Moléculaire d'Orsay, Université Paris-Sud

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1994年 / 59卷 / 02期

关键词：

D O I：

10.1021/jo00081a015

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Flash chromatography on silica gel of several sulfoxides of varying ee's shows a strong enantiomeric fractionation. For example (R)-methyl p-tolyl sulfoxide of 86% ee gives 99% ee (R) in the first fraction and 63% ee (R) in the last fraction, respectively, while (R)-ferrocenyl phenyl sulfoxide (65% ee) provides (S) enantiomer (19% ee) in the first fraction and (R) enantiomer (94% ee) in the last. fraction. Various aspects of the phenomena are discussed. This method provides a simple procedure to obtain high ee for sulfoxides prepared by asymmetric synthesis of only modest enantioselectivity.

引用

页码：370 / 373

页数：4

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