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DOI: 10.1055/s-0037-1609304
Synthesis of Monobactams via the Diastereoselective Kinugasa Reaction
Financial support for this work was provided through the National Science Center Grant OPUS 2015/17/B/STS/01011.Publikationsverlauf
Received: 20. November 2017
Accepted after revision: 19. Januar 2018
Publikationsdatum:
27. Februar 2018 (online)
Abstract
The Kinugasa reaction between phthalimidoacetylene and cyclic nitrones derived from l-phenylglycine or l-serine and glyoxylic acid, catalyzed by copper(I) chloride in the presence of triethylamine, is reported. The acetylene molecule approaches the nitrone exclusively anti to the bulky substituent next to the nitrogen atom to provide the cis-substituted β-lactam ring preferentially. The six-membered oxazinone ring can be easily opened, the phthaloyl residue can be transformed into a Boc protecting group, and substituents at the C-4 carbon atom and the nitrogen atom of the β-lactam ring can be easily removed or transformed into groups suitable for further synthesis of a variety of monobactam structures. Selected synthesized compounds were evaluated for their biological activity, showing interesting properties.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1609304.
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