Diastereoselective Ti-mediated preparation of bicyclic aminocyclopropanes from N-alkenyl amides

C Madelaine, AK Buzas, JA Kowalska-Six, Y Six…

Index: Madelaine, Claire; Buzas, Andrea K.; Kowalska-Six, Justyna A.; Six, Yvan; Crousse, Benoit Tetrahedron Letters, 2009 , vol. 50, # 38 p. 5367 - 5371

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Citation Number: 12

Abstract

Intramolecular Ti-mediated alkene–amide couplings of a range of N-alk-3-enyl amides fitted with a substituent at the homoallylic position are described. CF3-substituted compounds are suitable substrates and bicyclic aminocyclopropanes bearing a CF3 group can be prepared in this way. Good diastereoselectivities can be observed depending on the substitution pattern, and best results are obtained in diethyl ether rather than in THF.