Rhodium-catalyzed intramolecular hydroacylation of 1,2-disubstituted alkenes for the synthesis of 2-substituted indanones

摘要

The intramolecular hydroacylation of 1,2-disubstituted alkenes was considered to be a challenging task due to the side reactions resulted from the lack of additional substituent at 1-position and the low activity caused by the steric hindrance of substituent at 2-position, and an asymmetric version has not been considered possible due to problems associated with the racemization of the products. We have partially solved these problems. Catalyzed by an activated diphosphine-Rh complex and reacted in a selected dihalogenated solvent, the intramolecular hydroacylation of o-(2-arylvinyl)benzaldehydes provided the corresponding 2-aryl-1-indanones in high yields, and its asymmetric variant using o-(2-alkylvinyl) benzaldehydes afforded chiral 2-alkyl-1-indanones in high yields and with moderate enantioselectivities. (C) 2018 Elsevier Ltd. All rights reserved.