Peer-Reviewed Journal Details
Mandatory Fields
Ring, Aoife; Ford, Alan; Maguire, Anita R.
2016
Unknown
Tetrahedron Letters
Substrate and catalyst effects in C-H insertion reactions of a-Diazoacetamides
In Press
WOS: 16 ()
Optional Fields
C-H insertion Diazoacetamides Catalyst effects -lactams Gamma-lactams
Intramolecular CH insertion reactions of a-diazocarbonyl compounds typically proceed with preferential five-membered ring formation. However, the presence of a heteroatom such as nitrogen can activate an adjacent CH site toward insertion resulting in regiocontrol issues. In the case of a-diazoacetamide derivatives, both - and -lactam products are possible owing to this activating effect. Both - and -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 CH insertion reactions to form such compounds are attractive processes.Intramolecular CH insertion reactions of a-diazocarbonyl compounds typically proceed with preferential five-membered ring formation. However, the presence of a heteroatom such as nitrogen can activate an adjacent CH site toward insertion resulting in regiocontrol issues. In the case of a-diazoacetamide derivatives, both - and -lactam products are possible owing to this activating effect. Both - and -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 CH insertion reactions to form such compounds are attractive processes.
0040-4039
http://www.sciencedirect.com/science/article/pii/S0040403916314010http://www.sciencedirect.com/science/article/pii/S0040403916314010
10.1016/j.tetlet.2016.10.081
Grant Details