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- Title
Lithiated oxazolinyloxiranes and oxazolinylaziridines: key players in organic synthesis.
- Authors
Florio, Saverio; Degennaro, Leonardo; Mansueto, Rosmara; Musio, Biagia; Perna, Filippo M.; Salomone, Antonio
- Abstract
This paper focuses on α-lithiated oxazolinyloxiranes and oxazolinylaziridines, their generation, reactions, and synthetic applications. The ability of the oxazoline ring in providing stabilization to such α-heterosubstituted carbanions either through electronic effects and coordinative action has been stressed as well as the contribution to the configurational stability or instability of such species. IR spectroscopic data, multinuclear NMR investigations, and ab initio calculations planned to get insights on chemical properties and structural features have been carried out. A number of new reactions including alkylations, addition reactions, hydroxyalkylations, cyclopropanations, lactonizations, and rearrangements have been discovered, giving access to a variety of substances including: aziridinolactones, epoxylactones, aryl alkanones, polysubstituted cyclopropanes, cyclopropanefused lactones, dihydro-oxazoloisoquinolines, diversely functionalized oxazolines, and products that can be derived from them by synthetic elaboration.
- Subjects
OXAZOLINE; INFRARED spectroscopy; NUCLEAR magnetic resonance; ALKYLATION; CYCLOPROPANATION; CYCLOPROPANE; ADDITION reactions
- Publication
Pure & Applied Chemistry, 2014, Vol 86, Issue 6, p913
- ISSN
0033-4545
- Publication type
Article
- DOI
10.1515/pac-2013-1103