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Synlett 1991; 1991(1): 29-30
DOI: 10.1055/s-1991-20616
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A Convenient Synthesis of Methyl (p-Toluenesulphonylimino) acetate. Addition Reactions with Dienes

Peter Hamley* , Andrew B. Holmes, Alexander Kee, Tamara Ladduwahetty, David F. Smith
  • *University Chemical Laboratory, Lensfield Road, Cambridge CB2 1EW, England
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Publication Date:
07 March 2002 (online)

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The thermal reaction of methyl glyoxylate with p-toluenesulphonyl isocyanate gave the title imino-ester 1, which underwent in situ hetero-Diels-Alder reactions with various 1,3-dienes (6 examples). With 1-ethoxy-3-(trimethylsioxy)-1,3-cyclo-hexadiene the aza-Mukaiyama product was obtained exclusively, whereas with furans electrophilic substitution at the 2-position took place.

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