Stereo- and regiocontrol in intermolecular [2+2] cycloadditions between diarylketenes and allenamides to access substituted α-methylenecyclobutanones

Chem Commun (Camb). 2023 Sep 19. doi: 10.1039/d3cc03979j. Online ahead of print.ABSTRACTThe development of intermolecular [2+2] cycloadditions between allenamides and diarylketenes is described. α-Aryldiazo arylketones are employed as ketene precursors that react smoothly with allenamides in the presence of a P(C6F5)3 promoter. High diastereoselectivity (dr > 20 : 1) with endo-regioselectivity can be achieved when two aryl groups of ketenes have opposite electronic properties. The role of P(C6F5)3 is to increase the reaction yields, but also enhancing stereoselectivity.PMID:37724358 | DOI:10.1039/d3cc03979j

Source: Chemical Communications - September 19, 2023 Category: Chemistry Authors: Akshay Suresh Kshirsagar Sayaji Arjun More Rai-Shung Liu Source Type: research