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

doi:10.1055/s-1997-1366

Synthesis 1997; 1997(12): 1405-1410
DOI: 10.1055/s-1997-1366

paper

© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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

Abstract

PDF Download All articles of this category

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

PDF (645 kb)