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Synthesis 2013; 45(22): 3118-3124
DOI: 10.1055/s-0033-1338527
DOI: 10.1055/s-0033-1338527
paper
A Concise Cross-Metathesis Route to Enantiopure 1-Azaspirocycles
Further Information
Publication History
Received: 06 July 2013
Accepted after revision: 20 August 2013
Publication Date:
27 September 2013 (online)
We dedicate this manuscript to Adrian Blackman (University of Tasmania) and wish him well in his retirement.
Abstract
A concise synthesis of spiropyrrolidines and spiropiperidines has been developed. The approach employs a ruthenium–alkylidene-catalysed cross-metathesis reaction of enantiopure N-protected allylglycine with methylenecycloalkanes. The resultant alkene intermediates can then undergo a tandem acid-catalysed cyclisation to form spiropyrrolidines. Ring expansion of the spiropyrrolidine system, via an aziridinium intermediate, grants access to the homologous spiropiperidine ring system with excellent stereoretention.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
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