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Paper | Regular issue | Vol 51, No. 5, 1999, pp.1067-1071
Published online, 1st January, 1970
DOI: 10.3987/COM-99-8489
Highly Enantioselective Synthesis of 3-Hydroxy-2-phenylpiperidine via the Sharpless AD-Reaction

Heinz Stadler* and Michael Bös

*Pharma Division, Pharma Preclinical Research & Development, F.Hoffmann-La Roche Ltd., Grenzacherstrasse 124, CH-4070 Basel, Switzerland


Asymmetric dihydroxylation (AD) of the silyl enol ether (3) provided after hydrolysis the hydroxy ketone (4). Subsequent hydrogenation yielded the title compound (1) as a diastereomeric mixture. The cis-isomer is an important building block for the synthesis of potent NK1 receptor antagonists.