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

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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Synthetically useful asymmetric cross acyloin reactions with functionalized aliphatic aldehyde have a broad range of application. The products of acyloin reactions are α-hydroxy ketone which are the subunits in several compounds and can be found in many biologically important compounds. Phosphonates can be used as an intermediate in the synthesis of potentially significant peptide analogues, catalytic antibodies, and phosphonic acid-based antibiotics which are also acknowledged as biologically important com...
Citation Formats
S. Türkyılmaz, “Asymmetric solution-phase mixture aldol reaction using oligomeric ethylene glycol tagged chiral oxazolidinones,” TETRAHEDRON LETTERS, pp. 2031–2033, 2017, Accessed: 00, 2020. [Online]. Available: