2,6-Disubstituted and 2,2,6-Trisubstituted Piperidines from Serine: Asymmetric Synthesis and Further Elaboration

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...

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Bibliographic Details
Published in:Journal of organic chemistry 2010-08, Vol.75 (15), p.5223-5233
Main Authors: Acharya, Hukum P, Clive, Derrick L. J
Format: Article
Language:English
Subjects:
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Magnetic Resonance Spectroscopy
Organic chemistry
Oxidation-Reduction
Piperidines - chemical synthesis
Piperidines - chemistry
Preparations and properties
Serine - chemistry
Spectroscopy, Fourier Transform Infrared
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Summary: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo101010c