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Synthesis of sp3-rich chemical libraries based upon 1,2-Diazetidines
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Dean, Conor, Roesner, Stefan, Rajkumar, Sundaram, Clarkson, Guy J., Jones, Matthew and Shipman, Michael (2021) Synthesis of sp3-rich chemical libraries based upon 1,2-Diazetidines. Tetrahedron, 79 . 131836. doi:10.1016/j.tet.2020.131836 ISSN 0040-4020 .
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WRAP-Synthesis-sp3-rich-chemical-libraries-1-2-Diazetidines-Shipman-2020.pdf - Accepted Version - Requires a PDF viewer. Available under License Creative Commons Attribution Non-commercial No Derivatives 4.0. Download (1834Kb) | Preview |
Official URL: https://doi.org/10.1016/j.tet.2020.131836
Abstract
A strategy for the creation of sp3-rich, non-planar scaffolds for drug discovery is described. Stereocontrolled ring opening of homochiral 1,2-epoxides by hydrazine monohydrate followed by selective protection of both nitrogen atoms and Mitsunobu ring closure gives differentially protected, enantiomerically pure 1,2-diazetidines (up to 98% ee) bearing a variety of C-3 substituents. Iterative CāN functionalization at the two nitrogen atoms using a range of chemistries and coupling partners produces a 1,2-diazetidine based chemical library. Crystallographic data confirm that these frameworks display significant sp3-character with the nitrogen substituents adopting an anti-configuration.
| Item Type: | Journal Article | |||||||||
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| Subjects: | T Technology > TP Chemical technology | |||||||||
| Divisions: | Faculty of Science, Engineering and Medicine > Science > Chemistry | |||||||||
| Library of Congress Subject Headings (LCSH): | Hydrazine, Pharmaceutical technology, Pharmaceutical chemistry | |||||||||
| Journal or Publication Title: | Tetrahedron | |||||||||
| Publisher: | Pergamon | |||||||||
| ISSN: | 0040-4020 | |||||||||
| Official Date: | 22 January 2021 | |||||||||
| Dates: |
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| Volume: | 79 | |||||||||
| Article Number: | 131836 | |||||||||
| DOI: | 10.1016/j.tet.2020.131836 | |||||||||
| Status: | Peer Reviewed | |||||||||
| Publication Status: | Published | |||||||||
| Access rights to Published version: | Restricted or Subscription Access | |||||||||
| Date of first compliant deposit: | 1 December 2020 | |||||||||
| Date of first compliant Open Access: | 3 December 2021 | |||||||||
| RIOXX Funder/Project Grant: |
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