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Communication | Regular issue | Vol 24, No. 3, 1986, pp.621-624
Published online, 1st January, 1970
DOI: 10.3987/R-1986-03-0621
A Diadtereoselective Synthesis of threo 2-(α-Hydroxyalkyl)piperdines via Oxacarbamoylinium Ion-(Z)-vinylsilane Cyclization

Shinzo Kano,* Tsutomu Yokomatsu, Yoko Yuasa, and Shiroshi Shibuya

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


Reduction of 5-alkyl-N-(Z-4-silyl-3-butenyl)oxazolidine-2,4-diones (5a,b) with NaBH4, followed by cyclization with TiCl4 afforded the corresponding 1,8a-trans-1-alkyl-1,5,6,8a-tetrahydro-3H-oxazolo[3,4-a]pyridines (9a,b), respectively, with high diastereoselectivity. Catalytic hydrogenation of 9a, followed by alkaline hydrolysis gave threo 2-(α-hydroxyethyl)piperidine (12a). In a similar fashion, threo 2-(α-hydroxypropyl)piperidine (12b), (±)-β-conhydrine, was obtained from 9b.