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Communication | Special issue | Vol 30, No. 1, 1990, pp.263-266
Published online, 1st January, 1970
DOI: 10.3987/COM-89-S24
Diastereoselective Synthesis of 2,6-Disubstituted 3-Hydroxypiperidine, 2-(α-Hydroxyalkyl)-3-hydroxypiperidine and 2-(α-Hydroxyalkyl)-3-hydroxypyrrolidine Derivatives

Shinzo Kano,* Yoko Yuasa, Naoki Mochizuki, and Shiroshi Shibuya

*School of Pharmacy, Tokyo University of Pharmacy and Life Science, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan


Reduction of 5-substituted 5,8a-trans-oxazolo[3,4-a]pyridin-8-ones (7a,b), obtained by an application of α-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-trans-oxazolo[3,4-a]pyridin-8-one (7c) and pyrrolidine analogue (10) with NaBH4 and K-Selectride was also found to proceed with high diastereoselectivity.