A highly stereoselective synthesis of glycidic amides based on a new class of chiral sulfonium salts: applications in asymmetric synthesis.
A new type of chiral sulfonium salts that are characterized by a bicyclic system has been designed and synthesized from α-amino acids. Their corresponding ylides, which were prepared by basic treatment of the sulfonium salts, reacted smoothly with a broad array of simple and chiral aldehydes to provide trans-epoxy amides in reasonable to very good yields and excellent stereoselectivities (>98%). The obtained epoxy amides were found to be useful as synthetic building blocks. Thus, they were reduced into their corresponding epoxy alcohols and subjected to oxirane-ring-opening reactions with different types of nucleophiles.
Department of Organic Chemistry, Faculty of Sciences, University of Malaga, Campus de Teatinos s/n. 29071 Malaga, Spain. frsarabia@uma.es
Francisco
F
Sarabia
Carlos
C
Vivar-García
Miguel
M
García-Castro
Cristina
C
García-Ruiz
Francisca
F
Martín-Gálvez
Antonio
A
Sánchez-Ruiz
Samy
S
Chammaa
D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry; D000596:Amino Acids / Q000737:chemistry; D004852:Epoxy Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011422:Propionates / Q000138:chemical synthesis* / Q000737:chemistry; D012492:Salts / Q000737:chemistry; D013237:Stereoisomerism; D013452:Sulfonium Compounds / Q000138:chemical synthesis* / Q000737:chemistry
D000577:Amides; D000596:Amino Acids; D004852:Epoxy Compounds; D011422:Propionates; D012492:Salts; D013452:Sulfonium Compounds; C007869:glycidic acid