Acid-Promoted Retro-Mannich Reaction of N-Protected Tropenones to 2-Substituted Pyrroles

N‐protected tropenone 4 undergoes highly regioselective retro‐Mannich reactions to 2‐pyrrolyl ketones 5 and 7 in the presence of Lewis or Brønsted acids. Analogously, the pyrrole derivative 8a was obtained by using subsequent nucleophilic trapping with TMSCN. (© Wiley‐VCH Verlag GmbH & Co. KGaA,...

Full description

Saved in:
Bibliographic Details
Published in:European journal of organic chemistry 2004-04, Vol.2004 (7), p.1397-1400
Main Authors: Cramer, Nicolai, Juretschke, Jeannette, Laschat, Sabine, Baro, Angelika, Frey, Wolfgang
Format: Article
Language:English
Subjects:
Fragmentation
Ketones
Mannich reaction
Regioselectivity
Tropenones
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:N‐protected tropenone 4 undergoes highly regioselective retro‐Mannich reactions to 2‐pyrrolyl ketones 5 and 7 in the presence of Lewis or Brønsted acids. Analogously, the pyrrole derivative 8a was obtained by using subsequent nucleophilic trapping with TMSCN. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.200300804