1648931-34-3Relevant articles and documents
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
