Next Article in Journal
Polymeric Plant-derived Excipients in Drug Delivery
Next Article in Special Issue
Tris(2,4,6-trimethoxyphenyl)phosphine (TTMPP): Efficient Catalysts for the Cyanosilylation and Cyanocarbonation of Aldehydes and Ketones
Previous Article in Journal
Synthesis, Crystal Structure, and Kinetics of the Thermal Decomposition of the Nickel(II) Complex of the Schiff Base 2-[(4 Methylphenylimino)methyl]-6-methoxyphenol
Previous Article in Special Issue
Organocatalytic Oxidative Dehydrogenation of Dihydroarenes by Dioxygen Using 2,3-Dichloro-5,6-dicyano-benzoquinone (DDQ) and NaNO2
Molecules 2009, 14(7), 2594-2601; doi:10.3390/molecules14072594
Article

Calixpyrrole Derivatives: “Multi Hydrogen Bond” Catalysts for γ-Butenolide Synthesis

2
, 1
, 2,* , 1,* , 1 and 2
1 Department of Chemistry, University of Salerno, via Ponte don Melillo, 84084 Fisciano (SA), Italy 2 Department of Organic and Biological Chemistry, University of Messina, Salita Sperone 31, 98166 Messina, Italy
* Authors to whom correspondence should be addressed.
Received: 22 May 2009 / Revised: 7 July 2009 / Accepted: 9 July 2009 / Published: 15 July 2009
(This article belongs to the Special Issue Organocatalysis)
Download PDF [156 KB, uploaded 18 June 2014]

Abstract

Calix[4]pyrrole (1), calix[2]m-benzo[4]pyrrole (2), 10α,20β- and 10α,20α- bis(4-nitrophenyl)-calix[4]pyrroles 3 and 4, respectively, were found to exhibit various organocatalytic activities in the diastereoselective vinylogous addition reaction of 2-trimethylsilyloxyfuran (TMSOF, 7) to aldehydes. The γ-hydroxybutenolide products are obtained in fairly good yields and with moderate diastereoselectivity. The structures of the catalysts, as well as the reaction conditions, strongly influence the efficiency of the reaction.
Keywords: calixpyrroles; diastereoselective synthesis; organocatalysis; aldol addition; 2-Trimethyl-silyloxyfuran calixpyrroles; diastereoselective synthesis; organocatalysis; aldol addition; 2-Trimethyl-silyloxyfuran
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Share & Cite This Article

Export to BibTeX |
EndNote


MDPI and ACS Style

Cafeo, G.; De Rosa, M.; Kohnke, F.H.; Soriente, A.; Talotta, C.; Valenti, L. Calixpyrrole Derivatives: “Multi Hydrogen Bond” Catalysts for γ-Butenolide Synthesis. Molecules 2009, 14, 2594-2601.

View more citation formats

Related Articles

Article Metrics

Comments

Citing Articles

[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert