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 |
|---|---|
| Pages (from-to) | 5069-5072 |
| Number of pages | 4 |
| Journal | Tetrahedron Letters |
| Volume | 41 |
| Issue number | 26 |
| Publication status | Published - 2000 Jun 24 |
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Keywords
- 1,3-oxazolidine
- Diabetes
- Oxidative cleavage
- Solid phase synthesis
ASJC Scopus subject areas
- Biochemistry
- Organic Chemistry
- Drug Discovery
Cite this
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 journal › Article
}
TY - JOUR
T1 - Solid-phase synthesis of 1,3-oxazolidine derivatives
AU - Oh, Heong Sub
AU - Hahn, Hoh Gyu
AU - Cheon, Seung Hoon
AU - Ha, Deok-Chan
PY - 2000/6/24
Y1 - 2000/6/24
N2 - 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.
AB - 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.
KW - 1,3-oxazolidine
KW - Diabetes
KW - Oxidative cleavage
KW - Solid phase synthesis
UR - http://www.scopus.com/inward/record.url?scp=0141479914&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0141479914&partnerID=8YFLogxK
M3 - Article
AN - SCOPUS:0141479914
VL - 41
SP - 5069
EP - 5072
JO - Tetrahedron Letters
JF - Tetrahedron Letters
SN - 0040-4039
IS - 26
ER -