Lewis acid-catalyzed Diels-Alder reaction of 2-cyclopentenones with Danishefsky's diene: Double bond isomerization of tetrahydro-1Hindene- 1,5(7aH)-diones, and attempts on an asymmetric catalysis

Abstract

This work describes the investigation of the Diels-Alder reaction of the electron-rich diene trans- 1-methoxy-3-trimethylsilyloxy-1,3-butadiene (Danishefsky's diene) and the non-activated dienophiles 2-cyclopentenone and 2-methyl-2-cyclopentenone with respect to reactivity, regioselectivity and stereoselectivity. An observed double bond isomerization limits the practicability of 2-cyclopentenone as a dienophile in Diels-Alder reactions. 2-Methyl-2- cylopentenone could be converted quantitatively into one regioisomeric Diels-Alder adduct, however the stereochemical control turned out to be very demanding. © ARKAT-USA, Inc.