Understanding the Reactivity of Acyl Anion Equivalents: The Epoxide Ring Opening Case
Identifieur interne : 000705 ( Istex/Checkpoint ); précédent : 000704; suivant : 000706Understanding the Reactivity of Acyl Anion Equivalents: The Epoxide Ring Opening Case
Auteurs : Wilhelm A. Eger [Australie] ; Rebecca L. Grange [Australie] ; Heiko Schill [Australie] ; Régis Goumont [France] ; Timothy Clark [Allemagne] ; Craig M. Williams [Australie]Source :
- European Journal of Organic Chemistry [ 1434-193X ] ; 2011-05.
English descriptors
- KwdEn :
- Aaes, Acyl, Acyl anion equivalents, Acyl anions, Angew, Anion, Carbon atom, Chem, Corey, Dithiane, Engl, Epoxide, Epoxide ring opening, Epoxides, General rule, Lett, Negative charge, Negative hyperconjugation, Polarization effects, Seebach, Sulfur, Sulfur atom, Test vehicle, Tetrahedron, Tetrahedron lett, Tosmic, Verlag gmbh.
- Teeft :
- Aaes, Acyl, Acyl anion equivalents, Acyl anions, Angew, Anion, Carbon atom, Chem, Corey, Dithiane, Engl, Epoxide, Epoxide ring opening, Epoxides, General rule, Lett, Negative charge, Negative hyperconjugation, Polarization effects, Seebach, Sulfur, Sulfur atom, Test vehicle, Tetrahedron, Tetrahedron lett, Tosmic, Verlag gmbh.
Abstract
Acyl anion equivalents (umpolung) are the practitioner's first choice en route to 1,3‐hydroxy keto compounds from epoxides. Why? This investigation evaluates computationally and experimentally the reactivity of a near comprehensive range of acyl anion equivalents using epoxide ring opening as a test vehicle. Reactivity understanding, reactivity order, surprise failures in performance, along with unprecedented, but far from superior, reactivity of TosMIC is presented for the first time.
Url:
DOI: 10.1002/ejoc.201001680
Affiliations:
- Allemagne, Australie, France
- Bavière, District de Moyenne-Franconie, Île-de-France
- Erlangen, Versailles
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ISTEX:9E4FA57CF7F9E729032107FA7807769E2DB474C3Le document en format XML
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