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Fluorous “Racemic” Mixture Synthesis: Simultaneous Strategy for Demixing and Enantioseparation of Racemic Fluorous-Tagged Products

✍ Scribed by Takayuki Tonoi; Koichi Mikami

Publisher: John Wiley and Sons
Year: 2007
Tongue: English
Weight: 143 KB
Volume: 2007
Category: Article
ISSN: 1434-193X
DOI: 10.1002/ejoc.200700037

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✦ Synopsis

Abstract

Reported herein is the concept of fluorous “racemic” mixture synthesis (FRMS), which is applied to two types of proof‐of‐concept experiments. Mixtures of racemic O‐benzoylmandelate derivatives and prochiral crotonamide derivatives, respectively, bearing different lengths of fluorous‐cleavable tags are taken through a segmented reaction sequence to provide their enantiomers, as well as their individual derivatives, by virtue of chiral β‐cyclodextrin columns. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

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## Abstract The proof of concept experiments of fluorous “racemic” mixture synthesis (FRMS) is shown using polysaccharide‐based chiral stationary phases. The mixture of racemic __O__‐benzoylmandelate derivatives bearing different lengths of fluorous cleavable tags undergoes sequential reactions to