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


Turkyilmaz S. , Wilcox C. S.

TETRAHEDRON LETTERS, cilt.58, ss.2031-2033, 2017 (SCI İndekslerine Giren Dergi) identifier identifier identifier

  • Cilt numarası: 58 Konu: 21
  • Basım Tarihi: 2017
  • Doi Numarası: 10.1016/j.tetlet.2017.04.026
  • Dergi Adı: TETRAHEDRON LETTERS
  • Sayfa Sayıları: ss.2031-2033

Özet

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. (C) 2017 Elsevier Ltd. All rights reserved.