title: 3,4-Dihydroxypyrrolidines via modified tandem aza-Payne/hydroamination pathway.
abstract: The outcome of a tandem aza-Payne/hydroamination reaction is modified via the use of a latent nucleophile. The latter initially serves as an electrophile to intercept the aziridine alkoxide and afterward turns into a nucleophile thereby performing the aziridine ring opening, out competing the intramolecular aza-Payne pathway. Subsequent hydroamination in the same pot provides N-Ts enamide carbonates, which can be easily converted into biologically significant 3,4-dihydroxylactams.
authors: Department of Chemistry, Michigan State University , East Lansing, Michigan 48824, United States.
authors: Aman
authors: A
authors: Kulshrestha
authors: Nastaran
authors: N
authors: Salehi Marzijarani
authors: Kumar
authors: K
authors: Dilip Ashtekar
authors: Richard
authors: R
authors: Staples
authors: Babak
authors: B
authors: Borhan
mesh_terms: D000586:Amination; D001372:Aza Compounds / Q000737:chemistry*; D007769:Lactams / Q000737:chemistry*; D015394:Molecular Structure; D011759:Pyrrolidines / Q000737:chemistry*
chemical_list: D001372:Aza Compounds; D007769:Lactams; D011759:Pyrrolidines