Cyclizations using selenium chemistry for substituted 3-hydroxypiperidines and 3-hydroxypyrrolidines

Cooper, Matthew A. and Ward, A. David (2011) Cyclizations using selenium chemistry for substituted 3-hydroxypiperidines and 3-hydroxypyrrolidines. Australian Journal of Chemistry, 64 10: 1327-1338. doi:10.1071/CH11073

Author Cooper, Matthew A.
Ward, A. David
Title Cyclizations using selenium chemistry for substituted 3-hydroxypiperidines and 3-hydroxypyrrolidines
Journal name Australian Journal of Chemistry   Check publisher's open access policy
ISSN 0004-9425
Publication date 2011-08
Sub-type Article (original research)
DOI 10.1071/CH11073
Volume 64
Issue 10
Start page 1327
End page 1338
Total pages 12
Place of publication Collingwood, VIC, Australia
Publisher CSIRO Publishing
Collection year 2012
Language eng
Formatted 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.
Keyword N-Protected 3-Hydroxy-4-Pentenylamines
Electrophilic Olefin Heterocyclization
Induced Stereoselective Cyclization
Organocatalytic Michael Addition
Q-Index Code C1
Q-Index Status Confirmed Code
Institutional Status UQ

Document type: Journal Article
Sub-type: Article (original research)
Collections: Official 2012 Collection
Institute for Molecular Bioscience - Publications
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