Regioselective Functionalization of 1-Aza-1,3-Butadienes from Bis- and Mono(trimethylsilyl)-methylamine with Organocuprates

Bianca Flavia Bonini; Mariafrancesca Fochi; Mauro Comes Franchini; Germana Mazzanti; Alfredo Ricci; Jean-Paul Picard; Jacques Dunoguès; Jesus-Maria Aizpurua; Claudio Palomo

doi:10.1055/s-1997-1010

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

Abstract

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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

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