Asymmetric Catalysis. Asymmetric Catalytic Intramolecular Hydroacylation of 4-Pentenals Using Chiral Rhodium Diphosphine Catalysts

Abstract

Catalysts of the type [Rh(chiral diphosphine)] + convert 4-substituted 4-pentenals into the corresponding 3-substituted cyclopentanones with generally high turnover numbers and frequencies at 25 o C. The enantioselectivities of various substituted 4-pentenals with two chiral diphosphines have been explored. It was found that with the binap catalyst, almost complete enantioselectivity is observed for 4-pentenal substrates bearing 4-substituted tertiary substituents and for ester groups. Ketonic substituents give very high enantioselectivities