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Reactions of pyrrolidine enamines of cyclic and acyclic 3,4-dioxobutanoic acid Derivatives with dimethyl acetylenedicarboxylate. A new case of atropoisomerism.

✍ Scribed by Begoña de Ancos; M.Carmen Maestro; M.Rosano Martín; Ana I. Mateo

Publisher
Elsevier Science
Year
1994
Tongue
French
Weight
616 KB
Volume
50
Category
Article
ISSN
0040-4020

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✦ Synopsis

Dedicated to the memory of Ptvfiisor Francisco Far&z for his conttibntion to 5-alkoqfkn-2(5H)-ot~~ chanimy. Abetrack Reaction conditions and etmctutu of the. starting enmines (cyclic or opea-chain) determine greatly the tidal prcducta of the title rcactioos. Whemae io bemane and acetonitrile, DMAD and 1 give a mixture of the diiisomeric dieawhfs 5, in me&an01 they afford pirrobxiue 3. Enaminofhnumee 2 end 10 fond.& the cmqondiig 'Michael addocts" 7a,b,c and lla,b,c but fail to yield pimliziaes. It bes beea dmoa&&d that above b md c adductn differ exclusively on the amlqemmtofgmopeuoluldachirrluis.

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