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

Turkyilmaz S., Wilcox C. S.

TETRAHEDRON LETTERS, cilt.58, sa.21, ss.2031-2033, 2017 (SCI-Expanded) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 58 Sayı: 21
  • Basım Tarihi: 2017
  • Doi Numarası: 10.1016/j.tetlet.2017.04.026
  • Dergi Adı: TETRAHEDRON LETTERS
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.2031-2033
  • Anahtar Kelimeler: Solution-phase mixture synthesis, Oligomeric ethylene glycol, Evans aldol reaction, Oxazolidinone, Sorting tag, INDEXED COMBINATORIAL LIBRARY, FLUOROUS-TAGGING STRATEGY, STEREOISOMER LIBRARY, MULTIDRUG-RESISTANCE, NONNATURAL POLYENES, ORGANIC-SYNTHESIS, SORTING TAGS, AMINO-ACIDS, SEPARATION, CONDENSATIONS
  • Orta Doğu Teknik Üniversitesi Adresli: Evet

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.