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Regio- and stereocontrolled synthesis of 3-substituted 1,2-diazetidines by asymmetric allylic amination of vinyl epoxide
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Rajkumar, Sundaram, Clarkson, Guy J. and Shipman, Michael (2017) Regio- and stereocontrolled synthesis of 3-substituted 1,2-diazetidines by asymmetric allylic amination of vinyl epoxide. Organic Letters, 19 (8). pp. 2058-2061. doi:10.1021/acs.orglett.7b00653 ISSN 1523-7060.
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Official URL: http://doi.org/10.1021/acs.orglett.7b00653
Abstract
Pd-catalyzed asymmetric allylic amination of rac-vinyl epoxide with unsymmetrical 1,2-hydrazines proceeds with excellent regio- and stereocontrol, which after further ring closure provides differentially protected 3-vinyl-1,2-diazetidines in good yields. The chirality at Cā3 exerts stereocontrol over the nitrogen centers in the 1,2-diazetidine with all substituents orientat-ing themselves trans to their neighbours. Efficient functionalization without rupture of the strained ring is demonstrated (e.g. by cross-metathesis), establishing the first general route to Cā3 substituted 1,2-diazetidines in enantioenriched form.
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): | Chemistry, Organic, Heterocyclic compound, Organic compounds. | ||||||||
Journal or Publication Title: | Organic Letters | ||||||||
Publisher: | American Chemical Society | ||||||||
ISSN: | 1523-7060 | ||||||||
Official Date: | 21 April 2017 | ||||||||
Dates: |
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Volume: | 19 | ||||||||
Number: | 8 | ||||||||
Page Range: | pp. 2058-2061 | ||||||||
DOI: | 10.1021/acs.orglett.7b00653 | ||||||||
Status: | Peer Reviewed | ||||||||
Publication Status: | Published | ||||||||
Access rights to Published version: | Restricted or Subscription Access | ||||||||
Date of first compliant deposit: | 31 March 2017 | ||||||||
Date of first compliant Open Access: | 4 April 2018 | ||||||||
Funder: | Leverhulme Trust (LT), European Research Council (ERC) | ||||||||
Grant number: | RPG-2014-362, 637313 |
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