title: Synthesis of a potential intermediate for TMC-95A via an organocatalyzed aldol reaction.
abstract: N-Prolinylanthranilamide-based pseudopeptide organocatalyst 14 was shown to promote enantioselective direct aldol reaction of 7-iodoisatin and 2,2-dimethyl-1,3-dioxan-5-one with 90% conversion (75% isolated yield), 90% enantioselectivity, and 23:1 diastereoselectivity. To demonstrate the synthetic utility of this chemistry, the racemic aldol reaction product was converted in five steps to a potential intermediate for construction of the natural product TMC-95A.
authors.affiliation: Department of Chemistry, Case Western Reserve University , Cleveland, Ohio 44106, United States.
authors.forename: Anthony J
authors.initials: AJ
authors.lastname: Pearson
authors.forename: Santanu
authors.initials: S
authors.lastname: Panda
authors.forename: Scott D
authors.initials: SD
authors.lastname: Bunge