Solid-phase synthesis of 1,3-oxazolidine derivatives

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