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Synlett 1997; 1997(11): 1321-1323
DOI: 10.1055/s-1997-1010
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Regioselective Functionalization of 1-Aza-1,3-Butadienes from Bis- and Mono(trimethylsilyl)-methylamine with Organocuprates

Bianca Flavia Bonini1 , Mariafrancesca Fochi1 , Mauro Comes Franchini1 , Germana Mazzanti1 , Alfredo Ricci2 , Jean-Paul Picard3 , Jacques Dunoguès3 , Jesus-Maria Aizpurua4 , Claudio Palomo4
  • 1Dipartimento di Chimica Organica “A.Mangini”, Viale Risorgimento 4, I-40136 Bologna, Italy
  • 2Dipartimento di Chimica Organica “A.Mangini”, Viale Risorgimento 4, I-40136 Bologna, Italy, Fax +39 51 6443654; E-mail: ricci@ms.fci.unibo.it
  • 3Laboratoire de Chimie Organique et Organometallique (URA 35 CNRS), Université Bordeaux I, 3045 Talence, France
  • 4Departamento de Quimica Organica, Facultad de Quimica, Universidad del Pais Vasco, Apdo 1072, 20080 San Sebastian, Spain
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Publication History

Publication Date:
31 December 2000 (online)

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The addition of cuprates to 1-aza-1,3-butadienes from BSMA and MSMA occurs under mild conditions and with satisfactory yields in the presence of BF3/Et2O. The regioselectivity of the addition is closely related to the nature of the transferable ligand in the organometallic reagent. The possibility of performing a sequential C4-Nu followed by a C3-E bond formation in a one-pot/two-steps 'tandem' reaction is discussed as well.

1-aza-1,3-butadienes - functionalization - organocuprates