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4718640 
Journal Article 
Lewis acid-catalyzed Diels-Alder reaction of 2-cyclopentenones with Danishefsky's diene: double bond isomerization of tetrahydro-1H-indene-1,5(7aH)-diones, and attempts on an asymmetric catalysis 
Krebs, M; Laschat, S 
2012 
5-19 
WOS:000308692200002 
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. 
Diels-Alder reaction; Danishefsky's diene; cyclic enones; double bond isomerization