Solid-phase synthesis of 1,3-oxazolidine derivatives

Heong Sub Oh, Hoh Gyu Hahn, Seung Hoon Cheon, Deok Chan Ha

Research output: Contribution to journalArticle

24 Citations (Scopus)

Abstract

1,3-Oxazolidines 9 were synthesized by using a solid support. Regioselective ring opening of resin-bound epoxy ether 3 with ammonium chloride followed by nucleophilic substitution with sodium azide gave azido alcohol 7. Reduction of 7 provided 1-amino-2-alkanol 6, which was treated with various aldehydes and acyl chlorides or isocyanates to afford the corresponding 1,3-oxazolidines immobilized on Wang resin. Oxidative cleavage with DDQ from the solid support yielded 1,3-oxazolidines as a mixture of 10 (cis) and 11 (trans). (C) 2000 Elsevier Science Ltd.

Original languageEnglish
Pages (from-to)5069-5072
Number of pages4
JournalTetrahedron Letters
Volume41
Issue number26
DOIs
Publication statusPublished - 2000 Jun 24

Keywords

  • 1,3-oxazolidine
  • Diabetes
  • Oxidative cleavage
  • Solid phase synthesis

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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