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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
Received: 22 May 2009; in revised form: 7 July 2009 / Accepted: 9 July 2009 / Published: 15 July 2009
(This article belongs to the Special Issue Organocatalysis)
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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.

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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.

AMA Style

Cafeo G, De Rosa M, Kohnke FH, Soriente A, Talotta C, Valenti L. Calixpyrrole Derivatives: “Multi Hydrogen Bond” Catalysts for γ-Butenolide Synthesis. Molecules. 2009; 14(7):2594-2601.

Chicago/Turabian Style

Cafeo, Grazia; De Rosa, Margherita; Kohnke, Franz H.; Soriente, Annunziata; Talotta, Carmen; Valenti, Luca. 2009. "Calixpyrrole Derivatives: “Multi Hydrogen Bond” Catalysts for γ-Butenolide Synthesis." Molecules 14, no. 7: 2594-2601.



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