Article detail · 2010
Enantioselective Synthesis of Cyclic, Quaternary Oxonitriles
Journal
The Journal of Organic ChemistryISSN 0022-3263
The ISSN points to another catalog journal; the name is from the YÖKSİS record.
- Year
- 2010
- Type
- article
Data source split
- YÖKSİS YÖKSİS article record
- YÖKSİS venue The Journal of Organic Chemistry
- Catalog match (ISSN) Journal of Organic Chemistry
- OpenAlex OpenAlex enrichment (abstract, citations, topics)
Abstract
English (OpenAlex)
Quaternary oxonitriles are stereoselectively generated from the union of five-, six-, and seven-membered 2-chloroalkenecarbonitriles with chiral alcohols via a Claisen rearrangement. The strategy rests on a new conjugate addition-elimination of allylic alkoxides to 2-chlorocycloalkenecarbonitriles to afford substituted 2-alkoxyalkenenitriles. Subsequent thermolysis unmasks a cyclic oxonitrile while selectively forming a new quaternary center with enantiomeric ratios typically greater than 9:1. The overall alkylation strategy addresses the challenge of enantioselectively generating hindered, quaternary centers while simultaneously installing ketone, nitrile, and olefin functionalities.
Topics
- Asymmetric Synthesis and Catalysis
- Synthetic Organic Chemistry Methods
- Asymmetric Hydrogenation and Catalysis
Primary topic Asymmetric Synthesis and Catalysis