杯吡咯衍生物：用于合成γ-丁内酯的“多氢键”催化剂。

Calixpyrrole derivatives: "multi hydrogen bond" catalysts for gamma-butenolide synthesis.

作者信息

Cafeo Grazia, De Rosa Margherita, Kohnke Franz H, Soriente Annunziata, Talotta Carmen, Valenti Luca

机构信息

Department of Chemistry, University of Salerno, via Ponte don Melillo, 84084 Fisciano (SA), Italy.

出版信息

Molecules. 2009 Jul 15;14(7):2594-601. doi: 10.3390/molecules14072594.

DOI:10.3390/molecules14072594

PMID:19633626

原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6255108/

Abstract

Calix[4]pyrrole (1), calix[2]m-benzo[4]pyrrole (2), 10alpha,20beta- and 10alpha,20alpha- 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 gamma-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.

摘要

杯[4]吡咯（1）、杯[2]间苯并[4]吡咯（2）、10α,20β-和10α,20α-双（4-硝基苯基）-杯[4]吡咯3和4分别被发现，在2-三甲基硅氧基呋喃（TMSOF，7）与醛的非对映选择性烯醇式加成反应中表现出各种有机催化活性。γ-羟基丁烯内酯产物以相当高的产率和中等的非对映选择性得到。催化剂的结构以及反应条件对反应效率有很大影响。