Facial reconstruction

Search LJMU Research Online

Browse Repository | Browse E-Theses

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

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

Synthesis-sp3-rich-chemical-libraries-1-2-Diazetidines-Shipman-2020.pdf - Accepted Version
Available under License Creative Commons Attribution Non-commercial No Derivatives.

Download (1MB) | Preview


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
View Item View Item