Diastereoselective Synthesis of 2,6-Disubstituted 3-Hydroxypiperidine, 2-(a-Hydroxyalkyl)-3-hydroxypiperidine and 2-(a-Hydroxyalkyl)-3-hydroxypyrrolidine Derivatives
- 31 December 1989
- journal article
- research article
- Published by The Japan Institute of Heterocyclic Chemistry in HETEROCYCLES
- Vol. 30 (1) , 263-266
- https://doi.org/10.3987/com-89-s24
Abstract
Reduction of 5-substituted 5,8a-trans-oxazolo[3,4-a]pyridin-8-ones (7a,b), obtained by an application of .alpha.-acylamino radical cyclization at the initial stage, with NaBH4 and K-Selectride was found to proceed with complete stereocontrol in all cases. Reduction of 1-substituted, 1,8a-transoxazolo[3,4-a]pyridin-8-one (7c) and pyrrolidine analogue (10) with NaBH4 and K-Selectride was also found to proceed with high diastereoselectivity.Keywords
This publication has 2 references indexed in Scilit:
- .alpha.-Acylamino radical cyclizations: application to the synthesis of (-)-swainsonineThe Journal of Organic Chemistry, 1988
- Free radical cyclizations in alkaloid synthesis: (+)-heliotridine and (+)-hastanecineTetrahedron, 1985