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- Title
S2-type ring opening of substituted- N-tosylaziridines with zinc (II) halides: Control of racemization by quaternary ammonium salt.
- Authors
GHORAI, MANAS; TIWARI, DEO; KUMAR, AMIT; DAS, KALPATARU
- Abstract
Quaternary ammonium salt mediated highly regioselective ring opening of aziridines with zinc(II) halides to racemic and non-racemic β-halo amines in excellent yield and selectivity is described. The reaction proceeds via an S2-type pathway and the partial racemization of the starting substrate and the product was effectively controlled by using quaternary ammonium salts to afford the enantioenriched products (er up to 95:5). [Figure not available: see fulltext.]
- Subjects
RING-opening reactions; AZIRIDINES; ZINC halides; RACEMIZATION; CHEMICAL process control; QUATERNARY ammonium salts; LEWIS acids; NUCLEOPHILIC reactions
- Publication
Journal of Chemical Sciences, 2011, Vol 123, Issue 6, p951
- ISSN
0974-3626
- Publication type
Article
- DOI
10.1007/s12039-011-0178-0