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Synthesis and functionalization of 3-alkylidene-1,2-diazetidines using transition metal catalysis
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Brown, M. J. (Michael J.), Clarkson, Guy J., Inglis, Graham G. and Shipman, Michael. (2011) Synthesis and functionalization of 3-alkylidene-1,2-diazetidines using transition metal catalysis. Organic Letters, Volume 13 (Number 7). pp. 1686-1689. ISSN 1523-7060
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Official URL: http://dx.doi.org/10.1021/ol200193n
Abstract
An efficient two-step synthesis of a wide range of 3-methylene-1,2-diazetidines has been developed through application of a Cu(I)-catalyzed 4-exo ring closure. The double bond of this new class of strained heterocycle can be functionalized in a stereocontrolled manner by using palladium-catalyzed Heck reactions. Moreover, chemoselective reduction of 3-alkylidene-1,2-diazetidines gives access to saturated 1,2-diazetidines and vicinal diamines.
| Item Type: | Journal Article |
|---|---|
| Subjects: | Q Science > QD Chemistry |
| Divisions: | Faculty of Science > Chemistry |
| Library of Congress Subject Headings (LCSH): | Transition metal catalysts, Heterocyclic chemistry |
| Journal or Publication Title: | Organic Letters |
| Publisher: | American Chemical Society |
| ISSN: | 1523-7060 |
| Date: | 1 April 2011 |
| Volume: | Volume 13 |
| Number: | Number 7 |
| Page Range: | pp. 1686-1689 |
| Identification Number: | 10.1021/ol200193n |
| Status: | Peer Reviewed |
| Publication Status: | Published |
| Access rights to Published version: | Restricted or Subscription Access |
| Funder: | GlaxoSmithKline, Engineering and Physical Sciences Research Council (EPSRC), Advantage West Midlands (AWM), European Regional Development Fund (ERDF) |
| URI: | http://wrap.warwick.ac.uk/id/eprint/41310 |
Data sourced from Thomson Reuters' Web of Knowledge
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