Highly Stereoselective Halocyclopropanation of a,b-Unsaturated Amides

Highly Stereoselective Halocyclopropanation of a,b-Unsaturated Amides

A convenient highly stereoselective synthesis of chloro- and bromocyclopropanamides from di- tri- or tetrasubstituted (E)- or (Z)-,-unsaturated amides with total or high stereoselectivity promoted by chromium dichloride or dibromide is described. The transformation of chlorocyclopropanamides into th...

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Veröffentlicht in:Advanced synthesis & catalysis 2009-01, Vol.351 (13), p.2185-2198
Hauptverfasser: Concellon, Jose M, Rodriguez-Solla, Humberto, Blanco, Elena G, Villa-Garcia, Maria A, Alvaredo, Noemi, Garcia-Granda, Santiago, Diaz, M Rosario
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Sprache:eng
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Zusammenfassung:A convenient highly stereoselective synthesis of chloro- and bromocyclopropanamides from di- tri- or tetrasubstituted (E)- or (Z)-,-unsaturated amides with total or high stereoselectivity promoted by chromium dichloride or dibromide is described. The transformation of chlorocyclopropanamides into the corresponding ketones or amines is also reported. A mechanism to explain these transformations is proposed.
ISSN:1615-4150
DOI:10.1002/adsc.200900331