A Stereoselective [3+1] Ring Expansion for the Synthesis of Highly Substituted Methylene Azetidines. (1st September 2017)
- Record Type:
- Journal Article
- Title:
- A Stereoselective [3+1] Ring Expansion for the Synthesis of Highly Substituted Methylene Azetidines. (1st September 2017)
- Main Title:
- A Stereoselective [3+1] Ring Expansion for the Synthesis of Highly Substituted Methylene Azetidines
- Authors:
- Schmid, Steven C.
Guzei, Ilia A.
Schomaker, Jennifer M. - Abstract:
- Abstract: The reaction of rhodium‐bound carbenes with strained bicyclic methylene aziridines results in a formal [3+1] ring expansion to yield highly substituted methylene azetidines with excellent regio‐ and stereoselectivity. The reaction appears to proceed through an ylide‐type mechanism, where the unique strain and structure of the methylene aziridine promotes a ring‐opening/ring‐closing cascade that efficiently transfers chirality from substrate to product. The resultant products can be elaborated into new azetidine scaffolds containing vicinal tertiary‐quaternary and even quaternary‐quaternary stereocenters.
- Is Part Of:
- Angewandte Chemie. Volume 129:Number 40(2017)
- Journal:
- Angewandte Chemie
- Issue:
- Volume 129:Number 40(2017)
- Issue Display:
- Volume 129, Issue 40 (2017)
- Year:
- 2017
- Volume:
- 129
- Issue:
- 40
- Issue Sort Value:
- 2017-0129-0040-0000
- Page Start:
- 12397
- Page End:
- 12401
- Publication Date:
- 2017-09-01
- Subjects:
- Azetidine -- Aziridine -- Carbene -- Enantiospezifität -- Umlagerungen
Chemistry -- Periodicals
540 - Journal URLs:
- http://onlinelibrary.wiley.com/ ↗
- DOI:
- 10.1002/ange.201705202 ↗
- 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:
- 8637.xml