Dean, C ORCID: 0000-0002-1314-245X, Roesner, S
ORCID: 0000-0003-2143-4708, Rajkumar, S
ORCID: 0000-0003-2114-169X, Clarkson, GJ
ORCID: 0000-0003-3076-3191, Jones, M
ORCID: 0000-0002-6541-666X and Shipman, M
(2020)
Synthesis of sp3-rich chemical libraries based upon 1,2-diazetidines.
Tetrahedron, 79.
pp. 1-5.
ISSN 0040-4020
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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 C–N 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: | Article |
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Uncontrolled Keywords: | 0304 Medicinal and Biomolecular Chemistry; 0305 Organic Chemistry; Organic Chemistry |
Subjects: | Q Science > QD Chemistry R Medicine > RS Pharmacy and materia medica |
Divisions: | Pharmacy and Biomolecular Sciences |
Publisher: | Elsevier |
Date of acceptance: | 30 November 2020 |
Date of first compliant Open Access: | 23 April 2024 |
Date Deposited: | 23 Apr 2024 15:58 |
Last Modified: | 03 Jul 2025 12:37 |
DOI or ID number: | 10.1016/j.tet.2020.131836 |
URI: | https://researchonline.ljmu.ac.uk/id/eprint/23114 |
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