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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. doi:10.1021/ol200193n 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 | ||||
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Subjects: | Q Science > QD Chemistry | ||||
Divisions: | Faculty of Science, Engineering and Medicine > 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 | ||||
Official Date: | 1 April 2011 | ||||
Dates: |
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Volume: | Volume 13 | ||||
Number: | Number 7 | ||||
Page Range: | pp. 1686-1689 | ||||
DOI: | 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) |
Data sourced from Thomson Reuters' Web of Knowledge
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