Cathodically promoted stereoselective addition of 1,3-dinitro compounds tolevoglucosenone

This paper reports new applications of the cathodically promoted addition o f nitro compounds to the biomass-derived enone, levoglucosenone. A series o f 2-substituted 1,3-dinitropropanes were found to undergo addition to levog lucosenone with generation of a tricyclic product containing a fused cycloh exane system. The reaction yields are good to excellent and are catalyzed b y base (superoxide) generated electrochemically. Derivatives were prepared from 1,3-dinitropropane with the following. 2-substituents: 2-thienyl, 2-fu ryl, N-methyl-2-pyrryl, phenyl, 9-anthryl, and ferrocenyl. The structure of the derivative from 2-ferrocenyl-1,3-dinitropropane was established by X-r ay crystallography, thus confirming the NMR-based stereochemical assignment s of all of the other products. (C) 2000 The Electrochemical Society. S0013 -4651(99)09-019-9. All rights reserved.