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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
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: |
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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 | ||||||||
| Funder: | Leverhulme Trust (LT), European Research Council (ERC) | ||||||||
| Grant number: | RPG-2014-362, 637313 |
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