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The Lewis acid catalysed addition of 1-trimethylsilyl nitropropanate to imines

Anderson, JC; Peace, S; Pih, S; (2000) The Lewis acid catalysed addition of 1-trimethylsilyl nitropropanate to imines. SYNLETT (6) 850 - 852.

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Abstract

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

Type: Article
Title: The Lewis acid catalysed addition of 1-trimethylsilyl nitropropanate to imines
Keywords: amines, catalysis, diastereoselectivity, imines, samarium, ENANTIOSELECTIVE ADDITION, STEREOSELECTIVE SYNTHESIS, ORGANIC-SYNTHESIS, ALDEHYDES, HYDROXYLAMINES, NITROALKANES, DERIVATIVES, REDUCTION, SCANDIUM, NITROGEN
UCL classification: UCL > School of BEAMS > Faculty of Maths and Physical Sciences
UCL > School of BEAMS > Faculty of Maths and Physical Sciences > Chemistry
URI: http://discovery.ucl.ac.uk/id/eprint/80061
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