Premium
The Formal [3+2+1] Cyclisation of Cyclopropylamines with Carboxylic Anhydrides: A Quick Access to Polysubstituted 2,3,3a,4‐Tetrahydro6(5 H )‐indolone Ring Systems
Author(s) -
Larquetoux Laurent,
Kowalska Justyna A.,
Six Yvan
Publication year - 2004
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200400291
Subject(s) - chemistry , intramolecular force , cyclopropane , cyclopropanation , acylation , ring (chemistry) , diastereomer , carbonylation , bicyclic molecule , carboxylic acid , organic chemistry , intramolecular reaction , stereochemistry , medicinal chemistry , catalysis , carbon monoxide
Several 2‐azabicyclo[3.1.0]hexanes were synthesised using the intramolecular version of the Kulinkovich−de Meijere cyclopropanation reaction. Upon heating in the presence of a carboxylic anhydride, the cyclopropane rings of these systems open up to afford vinylogous amides. Depending on the reaction conditions used, the monoacylated compounds may be the major products, or subsequent acylation may take place to afford cyclic diketones. The method is flexible, and it is possible to incorporate different acyl groups in a two‐step sequence. The diketones are easily converted into 2,3,3a,4‐tetrahydro‐6(5 H )‐indolone derivatives by intramolecular aldolisation. The products, which are highly functionalised alcohols, are obtained as single diastereoisomers. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)