ChemInform Abstract: Diels‐Alder Reactions of Isoprene and 1,3‐Butadiene with Nitroheptenes Derived from Sugars.

Abstract

Diels-Alder Reactions of Isoprene and 1,3-Butadiene with Nitroheptenes Derived from Sugars.-The title reactions show an unlike stereoselectivity, as a consequence of the configuration of the adjacent chiral center to the dienophilic double bond. For isoprene adducts (III)-(VI), the favored regioisomers are those in which the nitro and the methyl groups on cyclohexene rings are in a 1,4-relationship. Treatment of (IIIa) with Bu3SnH/AIBN leads to the corresponding denitrated derivative. -(ROMAN, E.; BANOS, M.; GUTIERREZ, J. I.; SERRANO, J. A.; J.