Dean, C, Roesner, S, Rajkumar, S, Clarkson, GJ, Jones, M 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 & Biomolecular Sciences
Publisher:	Elsevier
SWORD Depositor:	A Symplectic
Date Deposited:	23 Apr 2024 15:58
Last Modified:	23 Apr 2024 16:00
DOI or ID number:	10.1016/j.tet.2020.131836
URI:	https://researchonline.ljmu.ac.uk/id/eprint/23114

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