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
Publication statusPublished - 2000 Jun 24

Fingerprint

Solid-Phase Synthesis Techniques
Derivatives
Epoxy Resins
Isocyanates
Ammonium Chloride
Sodium Azide
Aldehydes
Ether
Chlorides
Substitution reactions
Resins
Alcohols
oxazolidine

Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Oh, H. S., Hahn, H. G., Cheon, S. H., & Ha, D-C. (2000). Solid-phase synthesis of 1,3-oxazolidine derivatives. Tetrahedron Letters, 41(26), 5069-5072.

Solid-phase synthesis of 1,3-oxazolidine derivatives. / Oh, Heong Sub; Hahn, Hoh Gyu; Cheon, Seung Hoon; Ha, Deok-Chan.

In: Tetrahedron Letters, Vol. 41, No. 26, 24.06.2000, p. 5069-5072.

Research output: Contribution to journalArticle

Oh, HS, Hahn, HG, Cheon, SH & Ha, D-C 2000, 'Solid-phase synthesis of 1,3-oxazolidine derivatives', Tetrahedron Letters, vol. 41, no. 26, pp. 5069-5072.
Oh HS, Hahn HG, Cheon SH, Ha D-C. Solid-phase synthesis of 1,3-oxazolidine derivatives. Tetrahedron Letters. 2000 Jun 24;41(26):5069-5072.
Oh, Heong Sub ; Hahn, Hoh Gyu ; Cheon, Seung Hoon ; Ha, Deok-Chan. / Solid-phase synthesis of 1,3-oxazolidine derivatives. In: Tetrahedron Letters. 2000 ; Vol. 41, No. 26. pp. 5069-5072.
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