Premium
Chiral Brønsted Acid‐Catalyzed Asymmetric Synthesis of N ‐Aryl‐ cis ‐aziridine Carboxylate Esters
Author(s) -
Bew Sean P.,
Liddle John,
Hughes David L.,
Pesce Paolo,
Thurston Sean M.
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201611990
Subject(s) - chemistry , aziridine , catalysis , brønsted–lowry acid–base theory , alkyl , aryl , solvent , organic chemistry , enantioselective synthesis , combinatorial chemistry , carboxylate , optically active , ring (chemistry)
We report a multi‐component asymmetric Brønsted acid‐catalyzed aza‐Darzens reaction which is not limited to specific aromatic or heterocyclic aldehydes. Incorporating alkyl diazoacetates and, important for high ee's, ortho‐tert‐butoxyaniline our optimized reaction (i.e. solvent, temperature and catalyst study) affords excellent yields (61–98 %) and mostly >90 % optically active cis‐aziridines. (+)‐Chloramphenicol was generated in 4 steps from commercial starting materials. A tentative mechanism is outlined.