Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 19, Pages 5322-5326Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201611990
Keywords
asymmetric catalysis; aziridine; BrOnsted acids; multicomponent reactions
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Funding
- EPSRC GSK CASE award
- Engineering and Physical Sciences Research Council [EP/D500869/1] Funding Source: researchfish
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We report a multi-component asymmetric BrOnsted 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.
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