Synlett 2013; 24(15): 1949-1952
DOI: 10.1055/s-0033-1339486
letter
© Georg Thieme Verlag Stuttgart · New York

One-Pot Three-Component Barbier-Type Reaction for the Synthesis of β-Nitroamines

Authors

  • Raquel G. Soengas*

    Department of Chemistry & QOPNA, University of Aveiro, 3810-193 Aveiro, Portugal   Fax: +351(234)370084   eMail: artur.silva@ua.pt   eMail: rsoengas@ua.pt
  • Artur M. S. Silva*

    Department of Chemistry & QOPNA, University of Aveiro, 3810-193 Aveiro, Portugal   Fax: +351(234)370084   eMail: artur.silva@ua.pt   eMail: rsoengas@ua.pt
Weitere Informationen

Publikationsverlauf

Received: 24. Juni 2013

Accepted: 30. Juni 2013

Publikationsdatum:
07. August 2013 (online)


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Abstract

The combination of an aldehyde, bromonitromethane, and p-methoxyaniline in the presence of tin(II) chloride and titanium tetraethoxide allows a straightforward access to β-nitroamine derivatives. The use of solid paraformaldehyde results in the amino methylation of methylnitronate. On the other hand, chiral sugar-derived aldehydes furnished the corresponding nitrosugars in high yields and stereoselectivities.

Supporting Information