2,6-Disubstituted and 2,2,6-Trisubstituted Piperidines from Serine: Asymmetric Synthesis and Further Elaboration
journal contributionposted on 06.08.2010 by Hukum P. Acharya, Derrick L. J. Clive
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4-Hydroxy-3,4-dihydro-2H-pyridine-1-carboxylic acid benzyl esters, which are readily prepared from serine and terminal acetylenes, undergo Claisen rearrangement to piperidine derivatives when heated with butyl vinyl ether in the presence of Hg(OAc)2 and Et3N. This route to optically pure piperidines having substituents α to nitrogen is general, and the rearrangement products are versatile intermediates for making a broad range of amines containing a substituted piperidine subunit.