Chiral Brønsted Acid‐Catalyzed Asymmetric Synthesis of N‐Aryl‐cis‐aziridine Carboxylate Esters. (24th April 2017)
- Record Type:
- Journal Article
- Title:
- Chiral Brønsted Acid‐Catalyzed Asymmetric Synthesis of N‐Aryl‐cis‐aziridine Carboxylate Esters. (24th April 2017)
- Main Title:
- Chiral Brønsted Acid‐Catalyzed Asymmetric Synthesis of N‐Aryl‐cis‐aziridine Carboxylate Esters
- Authors:
- Bew, Sean P.
Liddle, John
Hughes, David L.
Pesce, Paolo
Thurston, Sean M. - Abstract:
- Abstract: 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.
- Is Part Of:
- Angewandte Chemie. Volume 129:Number 19(2017)
- Journal:
- Angewandte Chemie
- Issue:
- Volume 129:Number 19(2017)
- Issue Display:
- Volume 129, Issue 19 (2017)
- Year:
- 2017
- Volume:
- 129
- Issue:
- 19
- Issue Sort Value:
- 2017-0129-0019-0000
- Page Start:
- 5406
- Page End:
- 5410
- Publication Date:
- 2017-04-24
- Subjects:
- Asymmetrische Katalyse -- Aziridine -- Brønsted-Säuren -- Mehrkomponentenreaktionen
Chemistry -- Periodicals
540 - Journal URLs:
- http://onlinelibrary.wiley.com/ ↗
- DOI:
- 10.1002/ange.201611990 ↗
- Languages:
- English
- ISSNs:
- 0044-8249
- Deposit Type:
- Legaldeposit
- View Content:
- Available online (eLD content is only available in our Reading Rooms) ↗
- Physical Locations:
- British Library DSC - 0902.000000
British Library DSC - BLDSS-3PM
British Library HMNTS - ELD Digital store - Ingest File:
- 14511.xml