1195779-52-2Relevant academic research and scientific papers
A highly efficient methodology of asymmetric epoxidation based on a novel chiral sulfur ylide
Sarabia, Francisco,Chammaa, Samy,Garcia-Castro, Miguel,Martin-Galvez, Francisca
, p. 5763 - 5765 (2009)
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.
Exploring the reactivity of chiral glycidic amides for their applications in synthesis of bioactive compounds
Sarabia, Francisco,Vivar-Garcia, Carlos,Garcia-Ruiz, Cristina,Sanchez-Ruiz, Antonio,Pino-Gonzalez, Maria Soledad,Garcia-Castro, Miguel,Chammaa, Samy
, p. 3847 - 3867 (2014/06/24)
A new class of chiral sulfonium salts, derived from L- and D-methionine, has been designed and successfully employed in our laboratories for the diastereoselective synthesis of glycidic amides. The epoxy amides obtained were converted cleanly into 1,2-difunctionalized products through oxirane ring-opening reactions with different types of nucleophiles. The resulting ring-opened products represent valuable and useful building blocks for the synthesis of different bioactive products. Thus, the expedient synthesis of clavaminol H as well as the synthesis of key precursors for other bioactive compounds, for example, polyketide-derived natural products, have been achieved, demonstrating the synthetic efficiency and utility of this chemistry. The reactivity of chiral epoxy amides, efficiently prepared by a new asymmetric epoxidation methodology, has been explored through their reactions with various nucleophiles. The high regioselectivity and complete stereoselectivity observed for these ring-opening reactions were applied to the synthesis of bioactive compounds. Copyright
