Synthesis of sp3-rich chemical libraries based upon 1,2-diazetidines

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
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:	04 Jul 2025 12:45
DOI or ID number:	10.1016/j.tet.2020.131836
URI:	https://researchonline.ljmu.ac.uk/id/eprint/23114

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