Acid-promoted retro-Mannich reaction of N-protected tropenones to 2-substituted pyrroles

N-protected tropenone undergoes highly regioselective retro-Mannich reactions to 2-pyrrolyl ketones in the presence of Lewis or Bronsted acids. Analogously, a pyrrole deriv. was obtained by using subsequent nucleophilic trapping with trimethylsilanecarbonitrile. The possible Grob fragmentation of 3-oxo-8-azabicyclo[3.2.1]oct-6-ene-8-carboxylates and 8-[(4-methylphenyl)sulfonyl]-8-azabicyclo[3.2.1]oct-6-en-3-one was also investigated. The retro-Mannich reaction of 3-oxo-8-azabicyclo[3.2.1]oct-6-ene-8-carboxylic acid Me ester (I) in the presence of 4-methylbenzenesulfonic acid gave 2-(2-oxopropyl)-1H-pyrrole-1-carboxylic acid Me ester (II).


Published in:
European Journal of Organic Chemistry, 1397-1400
Year:
2004
Publisher:
Wiley-VCH Verlag GmbH & Co. KGaA
ISSN:
1434-193X
Keywords:
Note:
CAPLUS AN 2004:299604(Journal)
Laboratories:




 Record created 2011-08-17, last modified 2018-01-28


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