99267-80-8Relevant academic research and scientific papers
Approaches to the assembly-of the antifungal agent FR-900848: Studies on the asymmetric synthesis of bicyclopropanes and an X-ray crystallographic analysis of (4R,5R)-2-[(1R,3S,4S,6R)-6-phenyl-1-bicyclopropyl]-1,3- dimethyl-4,5-diphenylimidazolidine
Barrett,Doubleday,Tustin,White,Williams
, p. 1783 - 1784 (2007/10/02)
Both syn- and anti-bicyclopropane derivatives are efficiently prepared with good relative and absolute stereocontrol; structures are unequivocally determined by an X-ray crystallographic study of the title imidazolidine-derivative.
A Comparison of (Chloromethyl)- and (Iodomethyl)zinc Cyclopropanation Reagents
Denmark, Scott E.,Edwards, James P.
, p. 6974 - 6981 (2007/10/02)
A study comparing the rate of cyclopropanation of a range of olefins using (chloromethyl)- and (iodomethyl)zinc reagents is described.The (chloromethyl)zinc reagent derived from diethylzinc and chloroiodomethane is generally more reactive than the (iodomethyl)zinc analogue.The use of 1,2-dichloroethane as the solvent for these reactions was shown to be a crucial factor necessary to achieve clean, rapid, high-yielding cyclopropanations.The well-known directing effect of proximal oxygen substituents on the stereochemical outcome of "Simmons-Smith" cyclopropanations was shown to hold for the (chloromethyl)zinc reagent as well.The diethylzinc/chloroiodomethane reagent system in 1,2-dichloroethane should prove to be a valuable alternative to traditional (iodomethyl)zinc-based cyclopropanation reagents.
ASYMMETRIC SIMMONS-SMITH REACTIONS USING HOMOCHIRAL PROTECTING GROUPS
Mori, Atsunori,Arai, Isao,Yamamoto, Hisashi,Nakai, Hisao,Arai, Yoshinobu
, p. 6447 - 6458 (2007/10/02)
Asymmetric Simmons-Smith reactions of α,β-unsaturated acetals derived from chiral dialkyl tartrate or (2R,4R)-2,4-pentanediol are described.Treatment of the acetal with diethylzinc and methylene iodide gives a cyclopropane with high diastereoselectivity.The acetal group is readily transformed to the aldehyde or the ester group.In addition, the method is successfully applied to the enantioselective synthesis of 5,6-methanoleukotriene A4, a stable and selective inhibitor of leukotriene biosynthesis.
