Lithiated oxazolinyloxiranes and oxazolinylaziridines: key players in organic synthesis

Author:

Florio Saverio1,Degennaro Leonardo1,Mansueto Rosmara1,Musio Biagia2,Perna Filippo M.1,Salomone Antonio

Affiliation:

1. 1Dipartimento di Farmacia-Scienze del Farmaco, University of Bari Aldo Moro, via E. Orabona 4, 70125 Bari, Italy

2. 2Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge CB2 1EW, UK

Abstract

AbstractThis 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.

Publisher

Walter de Gruyter GmbH

Subject

General Chemical Engineering,General Chemistry

Reference29 articles.

1. a Synthesis;Florio;Chem Rev Chem Eur J,2012

2. Synthesis and Functionalisation of 2,3-Diheterocycle-Substituted Aziridines

3. For recent reviews of lithiated epoxide and aziridine chemistry see a Oxiranyl and aziridinyl anions as reactive intermediates in synthetic organic chemistry inAziridines and Epoxides in Organic Synthesis Weinheim see;Florio;Tetrahedron Synlett Pure Appl Chem Chem Rev,2003

4. a hooghe;Hu;Tetrahedron Chem Commun,2004

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