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Synthesis 1997; 1997(12): 1405-1410
DOI: 10.1055/s-1997-1366
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Diastereoselective Synthesis of Nonracemic 2-Alkyl-5-Hydroxypiperidines with (2R,5S)-Configuration via a Tandem Wittig [2+3] Cycloaddition Reaction. Synthesis of epi-Pseudoconhydrine and Its Homologs

Claus Herdeis* , Thomas Schiffer
  • *Institut für Pharmazie und Lebensmittelchemie, Universität Würzburg, D-97074 Würzburg, Am Hubland, Germany, Fax +49(931)8885462; E-mail: herdeis@pharmazie.uni-wuerzburg.de
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Publication Date:
31 December 2000 (online)

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A diastereoselective synthesis of cis-2-alkyl-5-hydroxypiperidines is presented, starting from enantiopure azidolactone 1. The key step of the reaction sequence is the tandem Wittig [2+3] cycloaddition reaction of lactol 2 to give triazolines 5a,b which are in equilibrium with the diazoamines 6a,b. Thermolysis of the mixture of 5 and 6 provides enantiopure 7, which is O-protected, diastereoselectively hydrogenated, and N-protected to 9. Further transformation of 9 yields epi-pseudoconhydrine (14) and its homologs.

cycloaddition reaction - Wittig reaction - tandem reaction