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

James C. Anderson; Simon Peace; Steven Pih

doi:10.1055/s-2000-6710

Synlett 2000; 2000(6): 0850-0852
DOI: 10.1055/s-2000-6710

letter

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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

Abstract

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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

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