✦ LIBER ✦

Solid-phase synthesis of 1,3-oxazolidine derivatives

✍ Scribed by Heong Sub Oh; Hoh-Gyu Hahn; Seung Hoon Cheon; Deok-Chan Ha

Publisher: Elsevier Science
Year: 2000
Tongue: French
Weight: 185 KB
Volume: 41
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)00775-9

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✦ Synopsis

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 aord 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).

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