Diastereo- and enantioselective synthesis of 4-nitrocyclohexanones by [4 + 2] cycloaddition of a chiral 2-aminobutadiene to nitralkenes

Article abstract of DOI:10.1055/s-1992-26349

The Diels-Alder reaction of 3-[(S)-2-(methoxymethyl)pyrrolidin-1-yl]-1,3-butadiene [(S)-3] with 2-aryl-1-nitroethenes afforded, after hydrolysis, the 5-aryl-2-methyl substituted 4-nitrocyclohexanones (R,S,R)-5 in excellent enantiomeric purities (ee = 95-99%) and with high diastereoselectivities (ds = 75-95%).