Synthesis 2014; 46(18): 2506-2514
DOI: 10.1055/s-0033-1338629
paper
© Georg Thieme Verlag Stuttgart · New York

A Novel Route to 6-Substituted Piperidin-3-ols via Domino Cyclization of 2-Hydroxy-6-phosphinyl-5-hexenyl Tosylates with Primary Amines: Synthesis of (±)-Pseudoconhydrine and (±)-epi-Pseudoconhydrine

Cathrin Scherner
a   Clausthal University of Technology, Institute of Organic Chemistry, Leibnizstrasse 6, 38678 Clausthal-Zellerfeld, Germany   Fax: +49(5323)722858   Email: ernst.schaumann@tu-clausthal.de
,
Jens-Kerim Ergüden
a   Clausthal University of Technology, Institute of Organic Chemistry, Leibnizstrasse 6, 38678 Clausthal-Zellerfeld, Germany   Fax: +49(5323)722858   Email: ernst.schaumann@tu-clausthal.de
,
Gunadi Adiwidjaja
b   University of Hamburg, Mineralogisch-Petrographisches Institut, Grindelallee 46, 20146 Hamburg, Germany
,
Ernst Schaumann*
a   Clausthal University of Technology, Institute of Organic Chemistry, Leibnizstrasse 6, 38678 Clausthal-Zellerfeld, Germany   Fax: +49(5323)722858   Email: ernst.schaumann@tu-clausthal.de
› Author Affiliations
Further Information

Publication History

Received: 02 March 2014

Accepted after revision: 04 April 2014

Publication Date:
23 June 2014 (online)


Abstract

2-Hydroxy-6-phosphinyl-5-hexenyl tosylates, oxirane ring-opening products derived from glycidyl tosylates and phosphinyl-substituted allyl anions, undergo domino SN2–Michael reactions with primary amines to give 6-phosphinylmethylpiperidin-3-ols. The phosphinyl unit can be used in Horner olefination reactions. This approach is applied to the synthesis of racemic pseudoconhydrine and its epimer.