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 language | English |
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Pages (from-to) | 5069-5072 |
Number of pages | 4 |
Journal | Tetrahedron Letters |
Volume | 41 |
Issue number | 26 |
DOIs | |
Publication status | Published - 2000 Jun 24 |
Keywords
- 1,3-oxazolidine
- Diabetes
- Oxidative cleavage
- Solid phase synthesis
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry