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3,4-Dihydroxypyrrolidines via Modified Tandem Aza-Payne/Hydroamination Pathway

Author:
Kulshrestha, Aman, Salehi Marzijarani, Nastaran, Dilip Ashtekar, Kumar, Staples, Richard, Borhan, Babak
Source:
Organic letters 2012 v.14 no.14 pp. 3592-3595
ISSN:
1523-7052
Subject:
Lewis acids, Lewis bases, carbonates, chemical reactions, chemical structure, ethyleneimine
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.
Agid:
5784062