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α-Acyl-α-diazoacetates in Transition-Metal-Free β-Lactam Synthesis

Judith Synofzik, Dmitry Dar'in, Mikhail S. Novikov, Grigory Kantin, Olga Bakulina and Mikhail Krasavin*

*Saint Petersburg State University, Saint Petersburg 199034, Russia, Email: m.krasavinspbu.ru

J. Synofzik, D. Dar'in, M. S. Novikov, G. Kantin, O. Bakulina, M. Krasavin, J. Org. Chem., 2019, 84, 12101-12110.

DOI: 10.1021/acs.joc.9b02030 (free Supporting Information)



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Abstract

Thermally promoted reactions of α-acyl-α-diazoacetates with imines deliver α-alkoxycarbonyl-substituted β-lactams with outstanding diastereoselectivity. DFT calculations revealed the occurence of 1,3-oxazin-4-one intermediates.


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Key Words

β-Lactams


ID: J42-Y2019