Cyclopropanation of Various Substrates via Simmons-Smith and Michael-Initiated Ring Closure (MIRC) Reactions

摘要: Cyclopropanation of various electron rich and deficient olefins via Simmons-Smith Michael-initiated ring closure reactions was studied in our research. Cinnamyl alcohol 18 succesfully cyclopropanated a good to excellent yield using reactions. Methyl benzyl crotonate 14 16 were labile MIRC reaction condition indicated by the detection starting material degradation NMR spectra crude reactions, allowed low moderate product yield. The other materials, i.e., cinnamaldehyde 19 , methyl cinnamate 20 mono- di-protected cross-coupled (4 R ,5 E )-methyl 5-( tert -butyldimethylsilyloxy)-4-hydroxyhepta-2,6-dienoate 25 -butyldimethylsilyloxy)-4-(methoxymethoxy)hepta-2,6-dienoate 26 apparently incompatible set study.