Synthesis of 1,3-Disubstituted Azetidines via a Tandem Ring-Opening Ring-Closing Procedure

Abstract

The synthesis of N-substituted symmetrical azetidines has been achieved in high yields via the reaction of primary amines undergoing an epoxide ring-opening reaction followed by an in situ ring-closing step.

Key words

azetidines - tertiary alcohols - azo compounds - cyclization - tandem reaction

• References and Notes

• 1 Couty F, Evano G. Synlett 2009; 3053
• 2 March-Cortijos A, Snape TJ. Tetrahedron: Asymmetry 2008; 19: 1761
• 3 March-Cortijos A, Snape TJ. Org. Biomol. Chem. 2009; 7: 5163
• 4 Compound 1 is prepared by the method mentioned above in the text from a precursor synthesised in ref. 2 and 3
• 5 Corey EJ, Marfat A, Goto G, Brion F. J. Am. Chem. Soc. 1980; 102: 7984
• 6 Hart T, Macias AT, Benwell K, Brooks T, D’Alessandro J, Dokurno P, Francis G, Gibbons B, Haymes T, Kennett G, Lightowler S, Mansell H, Matassova N, Misra A, Padfield A, Parsons R, Pratt R, Robertson A, Walls S, Wong M, Roughley S. Bioorg. Med. Chem. Lett. 2009; 19: 4241
• 7 Roughley SD, Hart T. Tetrahedron Lett. 2010; 51: 5191
• 8 Baldwin JE. J. Chem. Soc., Chem. Commun. 1976; 734
• 9 Hillier MC, Chen CY. J. Org. Chem. 2006; 71: 7885
• 10 Ju YH, Varma RS. J. Org. Chem. 2006; 71: 135
• 11 Toda T, Karikomi M, Ohshima M, Yoshida M. Heterocycles 1992; 33: 511
• 12 Jung ME, Piizzi G. Chem. Rev. 2005; 105: 1735
• 13 CCDC 840439 (7) and CCDC 840438 (8) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/data_request/cif, or by emailing [e-mail], or by contacting The Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; fax: [phone]