Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

Cyclizations using Selenium Chemistry for Substituted 3-Hydroxypiperidines and 3-Hydroxypyrrolidines

Matthew A. Cooper A B C and A. David Ward B
+ Author Affliations
- Author Affliations

A Institute for Molecular Bioscience, The University of Queensland, St Lucia, Qld 4072, Australia.

B Department of Chemistry, University of Adelaide, Adelaide, SA 5005, Australia.

C Corresponding author. Email: m.cooper@uq.edu.au

Australian Journal of Chemistry 64(10) 1327-1338 https://doi.org/10.1071/CH11073
Submitted: 14 February 2011  Accepted: 27 April 2011   Published: 23 August 2011

Abstract

The development of new methods for the stereoselective synthesis of nitrogen heterocycles is of current interest because of increasing demands for the syntheses of biologically important alkaloids and related compounds. It is shown that selenium-induced cyclization of 4-hydroxy-5-pentenylamines occurs regio- and stereo-selectively to afford cis-3-hydroxy-2-phenylselenomethylpyrrolidines, whereas 5-hydroxy-6-hexenylamines cyclize and give trans-3-hydroxy-2-phenylselenomethylpiperidines, with some compounds forming stable hydrates. In all cases cyclization proceeds regioselectively to give only the exo adducts with moderate to good diastereoselectivity. The reaction appeared to be under kinetic control as product ratios did not alter with time and the separated diastereomers did not interconvert when resubjected to the reaction conditions. These phenylseleno-substituted compounds could be transformed to diols by substitution of the corresponding selenone with a hydroxide ion. Substituted pyrrolidines and piperidines were thus afforded from unsaturated protected amines by electrophilic activation with SeII, followed by oxidation of the intermediate to SeVI and substitution with nucleophiles.


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