Substrate and catalyst effects in C-H insertion reactions of α-diazoacetamides

Ring, Aoife; Ford, Alan; Maguire, Anita R.

Substrate and catalyst effects in C-H insertion reactions of α-diazoacetamides

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Accepted Version

Date

2016-10-22

Authors

Ring, Aoife

Ford, Alan

Maguire, Anita R.

Publisher

Elsevier

Published Version

10.1016/j.tetlet.2016.10.081

Abstract

Intramolecular C–H insertion reactions of α-diazocarbonyl compounds typically proceed with preferential five-membered ring formation. However, the presence of a heteroatom such as nitrogen can activate an adjacent C–H site toward insertion resulting in regiocontrol issues. In the case of α-diazoacetamide derivatives, both β- and γ-lactam products are possible owing to this activating effect. Both β- and γ-lactam products are powerful synthetic building blocks in the area of organic synthesis, as well as a common scaffold in a range of natural and pharmaceutical products and therefore C–H insertion reactions to form such compounds are attractive processes.

Keywords

C-H insertion , Diazoacetamides , Catalyst effects , Gamma-lactams , ß-lactams

Citation

Ring, A., Ford, A. and Maguire, A. R. (2016) 'Substrate and catalyst effects in C–H insertion reactions of α-diazoacetamides', Tetrahedron Letters, 57(49), pp. 5399-5406.