93906-79-7Relevant academic research and scientific papers
Studies on Chiral Organo-Sulfur Compounds. II. Stereochemistry of Thermal Chiral Allyl Sulfinate-Sulfone Rearrangements
Hiroi, Kunio,Kitayama, Ryuichi,Sato, Shuko
, p. 2628 - 2638 (2007/10/02)
A highly efficient and general synthetic route to optically active sulfinates by the stereospecific boron trifluoride etherate-catalyzed esterification of sulfinamides was developed.Dramatic solvent effects were observed in the thermal transformation of allyl sulfinate derivatives to sulfones.Heating of chiral trans- and cis-allyl sulfinates, (S)-(-)-3a,c,e and (S)-(-)-3b,d,f, in N,N-dimethylformamide at 90-120 deg C provided chiral sulfones (S)-(+)- and (R)-(-)-5,6,7 in good yields, respectively, with exceedingly high stereospecificity. Keywords - asymmetric transfer; stereospecificity; chiral allyl sulfinate; chiral allyl sulfone; boron trifluoride etherate; thermolysis
