Asymmetric Solution-phase Mixture Aldol Reaction Using Oligomeric Ethylene Glycol Tagged Chiral Oxazolidinones

Overview

Journal Tetrahedron Lett

Publisher Elsevier

Specialty Chemistry

Date 2017 Oct 24

PMID 29056780

Citations 3

Authors

Serhan Turkyilmaz

Craig S Wilcox

Affiliations

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Abstract

Sorting tags are oligomeric structures that can be used as protecting groups or chiral auxiliaries enabling solution-phase mixture syntheses of multiple tagged compounds in one pot and allowing for facile and predictable chromatographic separation of products at the end of synthetic sequences. Perfluorinated hydrocarbon and oligomeric ethylene glycol (OEG) derivatives are known classes of sorting tags. Herein we describe the preparation of OEGylated chiral oxazolidinones and their use in asymmetric solution-phase mixture aldol reactions. Through the use of such oxazolidinones based on tyrosine four different individually tagged aldol adducts were obtained as a mixture, chromatographically demixed, detagged, and it was shown that these processes gave the desired aldol products in good yield and enantioselectivity.

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Asymmetric solution-phase mixture aldol reaction using oligomeric ethylene glycol tagged chiral oxazolidinones.

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