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

Molecules

Grazia Cafeo²  Margherita De Rosa¹  Franz H. Kohnke²  Annunziata Soriente¹  Carmen Talotta¹ 

[1] Department of Chemistry, University of Salerno, via Ponte don Melillo, 84084 Fisciano (SA), Italy; E-mail:;Department of Organic and Biological Chemistry, University of Messina, Salita Sperone 31, 98166 Messina, Italy; E-mails:

关键词: calixpyrroles;    diastereoselective synthesis;    organocatalysis;    aldol addition;    2-Trimethyl-silyloxyfuran;   

DOI  :  10.3390/molecules14072594

来源: mdpi

【 摘 要 】

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.

【 授权许可】

CC BY   
© 2009 by the authors; licensee Molecular Diversity Preservation International, Basel, Switzerland.