Stereoselective synthesis and applications of nitrogen substituted donor-acceptor cyclopropanes (N-DACs) in the divergent synthesis of azacycles

A new, highly stereoselective intramolecular cyclopropanation of vinylogous carbamates with carbenes in the presence of Cu(acac)(2) as the catalyst has been developed for the construction of cyclopropapyrrolidinones. The 'syn' isomer of N-DAC can be converted to the 'anti' isomer...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2012-03, Vol.10 (9), p.1735-1738
Main Authors: Gharpure, Santosh J, Vijayasree, U, Reddy, S Raja Bhushan
Format: Article
Language:English
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Summary:A new, highly stereoselective intramolecular cyclopropanation of vinylogous carbamates with carbenes in the presence of Cu(acac)(2) as the catalyst has been developed for the construction of cyclopropapyrrolidinones. The 'syn' isomer of N-DAC can be converted to the 'anti' isomer by simple silica gel treatment. Regioselective cleavage of each of the cyclopropane bonds of these two acceptor substituted N-DACs led to a diverse array of azacycles.
ISSN:1477-0520
1477-0539
DOI:10.1039/c2ob06591f