MgI2-Mediated Ring Expansions of Secondary Methylenecyclopropyl Amides
- 15 March 2003
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 125 (14) , 4028-4029
- https://doi.org/10.1021/ja028967l
Abstract
Ring expansion of secondary methylenecyclopropyl amides in the presence of MgI2 was investigated. Various isomeric five-membered unsaturated lactams were obtained, depending on the character of the substituent Q. The amide group served as a nucleophile in ring closing as well as an activator for ring opening. In the presence of a variety of aryl aldimines or aldehydes, alkylative ring expansion occurred in a single step under mild and neutral conditions leading to gamma'-amino- or -hydroxy-alkylated pyrrol-2-ones. Also, it was shown that a 4-methylpyrrol-2-one could be transformed to a gamma-hydroxy-alkylated product by the use of a direct vinylogous aldol reaction.Keywords
This publication has 15 references indexed in Scilit:
- α-(N-Carbamoyl)alkylcuprate Chemistry in the Synthesis of Nitrogen HeterocyclesThe Journal of Organic Chemistry, 2002
- 5-exo Atom transfer cyclisation onto alkynes mediated by copper(I) complexesTetrahedron Letters, 2001
- Direct vinylogous aldol addition of γ-butyrolactones and γ-butyrolactamsTetrahedron Letters, 2000
- The synthetic utility of furan-, pyrrole- and thiophene-based 2-silyloxy dienesChemical Society Reviews, 2000
- Stereocontrolled Total Synthesis of (+)-K252aJournal of the American Chemical Society, 1999
- Synthesis of Methylene- and Alkylidenecyclopropane DerivativesChemical Reviews, 1998
- N-sulfonyl imines — Useful synthons in stereoselective organic synthesisPublished by Springer Nature ,1997
- New synthesis of nitrogen heterocycles through amide-directed hydrocarbonylation of alkenamides catalyzed by rhodium complexesThe Journal of Organic Chemistry, 1991
- New protocols for the synthesis of substituted 4-O-methyl tetramatesJournal of the Chemical Society, Perkin Transactions 1, 1990
- Intramolecular Diels-Alder reactions. 12. Competitive [4 + 2] and [2 + 2] cycloadditions of N-(phenylpropargyl)-cis-cinnamamideThe Journal of Organic Chemistry, 1976