74185-86-7Relevant academic research and scientific papers
Visible-Light-Induced Cycloaddition of α-Ketoacylsilanes with Imines: Facile Access to β-Lactams
Ye, Jian-Heng,Bellotti, Peter,Paulisch, Tiffany O.,Daniliuc, Constantin G.,Glorius, Frank
supporting information, p. 13671 - 13676 (2021/05/11)
We report the synthesis of β-lactams from α-ketoacylsilanes and imines, which proceeds via a formal [2+2] photochemical cycloaddition with in situ generation of siloxyketene. This mild and operationally simple reaction proceeds in an atom-economic fashion with broad substrate scope, including aldimines, ketimines, hydrazones, and fused nitrogen heterocycles, affording a variety of important β-lactams with satisfactory diastereoselectivities in most cases. This reaction also features good functional-group tolerance, facile scalability and product diversification. Experimental and computational studies suggest that α-ketoacylsilanes can serve as photochemical precursors by engaging in a 1,3 silicon shift to the distal carbonyl group.
STEREOSELECTIVE ANNELATION OF TRIMETHYLSILOXYACETIC ACIDS AND IMINES INTO 3-HYDROXY-β-LACTAMS
Cossio, Fernando P.,Palomo, Claudio
, p. 4239 - 4242 (2007/10/02)
Stereoselective synthesis of variously substituted 3-hydroxy-β-lactams can be achieved by the annelation of Schiff bases with trimethylsiloxyacetic acids promoted by phenyl dichlorophosphate reagent.A potential synthesis of N-unsubstituted β-lactams is ma
