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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

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Official URL: http://doi.org/10.1021/acs.orglett.7b00653

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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 C–3 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 C–3 substituted 1,2-diazetidines in enantioenriched form.

Item Type: Journal Article
Subjects: Q Science > QD Chemistry
Divisions: Faculty of 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:
DateEvent
21 April 2017Published
4 April 2017Available
30 March 2017Accepted
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
Funder: Leverhulme Trust (LT), European Research Council (ERC)
Grant number: RPG-2014-362, 637313

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