169301-33-1Relevant articles and documents
DIELS-ALDER REACTIONS OF ISOPRENE AND 1,3-BUTADIENE WITH NITROHEPTENES DERIVED FROM SUGARS
Roman, Emilio,Banos, Manuel,Gutierrez, Juan I.,Serrano, Jose A.
, p. 703 - 722 (2007/10/02)
The Diels-Alder cycloadditions of 1,3-butadiene and isoprene with D-galacto- and D-manno-(E)-nitroalkenes are described.These reactions showed an unlike stereoselectivity, as a consequence of the configuration of the adjacent chiral centre to the dienophilic double bond.For isoprene adducts, the favored regioisomers were those in which the nitro and the methyl groups on cyclohexene rings are in a 1,4-relationship.Assignment of absolute configurations at the new chiral centres in the adducts were based on NMR data and polarimetric correlations with known compounds.
Asymmetric Diels-Alder Reactions of a Chiral Sugar Nitroalkene: Diastereofacial Selectivity and Regioselectivity
Serrano, Jose A.,Caceres, Luis E.,Roman, Emilio
, p. 941 - 942 (2007/10/02)
The uncatalysed Diels-Alder addition of 1-(trimethylsilyloxy)- and 1-acetoxybuta-1,3-diene to a sugar-derived nitroalkene proceeds with complete regioselectivity and diastereofacial selectivity to yield crystalline, optically pure, cyclohexene derivatives