Aluminum chloride-mediated acylation of methylenecyclobutanes. A facile synthetic protocol for the construction of substituted cyclopentenes
- PMID: 18452302
- DOI: 10.1021/ol8006502
Aluminum chloride-mediated acylation of methylenecyclobutanes. A facile synthetic protocol for the construction of substituted cyclopentenes
Abstract
Reactions of methylenecyclobutanes (MCBs) with acyl chlorides produce the corresponding substituted cyclopentene derivatives in moderate to high yields via ring enlargement in the presence of aluminum chloride under mild conditions. A plausible mechanism has been proposed on the basis of control and deuterium labeling experiments.
Similar articles
-
Reactions of monoaryl-substituted methylenecyclobutanes and methylenecyclopropanes with 1-hydroxybenzotriazole (HOBt), 1-hydroxy-7-azabenzotriazole (HOAt), and 1-hydroxysuccinimide (HOSu).J Org Chem. 2009 Mar 20;74(6):2516-20. doi: 10.1021/jo9000299. J Org Chem. 2009. PMID: 19222218
-
A synthetic protocol of trans-substituted cyclopentenes via the ring-opening rearrangement of MCP alkenyl derivatives.J Org Chem. 2010 Feb 5;75(3):902-5. doi: 10.1021/jo902512q. J Org Chem. 2010. PMID: 20070097
-
Acylation of alkylidenecyclopropanes for the facile synthesis of alpha,beta-unsaturated ketone and benzofulvene derivatives with high stereoselectivity.Org Lett. 2007 Apr 26;9(9):1667-70. doi: 10.1021/ol070331h. Epub 2007 Mar 27. Org Lett. 2007. PMID: 17385872
-
Acetoxylation and hydroxylation of diarylmethylenecycloalkanes via radical approach.J Org Chem. 2010 Apr 16;75(8):2528-33. doi: 10.1021/jo9027209. J Org Chem. 2010. PMID: 20329791
-
Palladium-catalyzed ring enlargement of aryl-substituted methylenecyclopropanes to cyclobutenes.J Am Chem Soc. 2006 Jun 14;128(23):7430-1. doi: 10.1021/ja061749y. J Am Chem Soc. 2006. PMID: 16756283
LinkOut - more resources
Full Text Sources