866208-16-4Relevant academic research and scientific papers
Cyclic sulfur ylides derived from gleason-type chiral auxiliaries for the asymmetric synthesis of epoxy amides
Sarabia, Francisco,Vivar-Garcia, Carlos,Garcia-Castro, Miguel,Martin-Ortiz, Jorge
, p. 3139 - 3150 (2011/06/22)
Gleason-type chiral auxiliaries were used for the synthesis of a novel class of sulfonium salts, obtained via methylation of the sulfide with Meerwein's salt. The salts were reacted with aldehydes under basic conditions to provide epoxy amides, which were reduced to their corresponding epoxy alcohols in excellent enantiomeric excesses. Interestingly, it was feasible to synthesize both enantiomeric epoxy alcohols depending on which of the sulfonium salts, prepared from L-amino acids (6 and 9 from L-valine or 15 and 16 from L-serine) was employed.
A highly efficient methodology of asymmetric epoxidation based on a novel chiral sulfur ylide
Sarabia, Francisco,Chammaa, Samy,Garcia-Castro, Miguel,Martin-Galvez, Francisca
supporting information; experimental part, p. 5763 - 5765 (2010/01/31)
A new type of chiral sulfur ylides has been synthesized and their reactivities against carbonyl compounds tested, showing a high degree of stereoselectivity in the formation of trans epoxy amides under very mild reaction conditions.
