Download PDF
Synlett 2000; 2000(6): 0850-0852
DOI: 10.1055/s-2000-6710
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

The Lewis Acid Catalysed Addition of 1-Trimethylsilyl Nitropropanate to Imines

James C. Anderson* , Simon Peace, Steven Pih
  • *Department of Chemistry, University of Nottingham, Nottingham, NG7 2RD, UK; Fax +44(0)115 951 3564; E-mail: j.anderson@sheffield.ac.uk
Further Information

Publication History

Publication Date:
31 December 2000 (online)

  PDF Download  Permissions and Reprints All articles of this category

The scandium triflate catalysed addition of 1-trimethylsilyl nitropropanate to aryl and alkyl imines is described. The use of N-(4-methoxyphenyl)imines gave superior yields and/or diastereoselectivities of β-nitro amines in most cases examined. The product β-nitro amines can be readily manipulated to 1,2-diamines by samarium diiodide reduction, formation of the cyclic urea and removal of the 4-methoxyphenyl group with ceric ammonium nitrate.

amines - catalysis - diastereoselectivity - imines - samarium