三氟甲磺酸钪催化富电子苯酚与给体-受体环丙烷的[4 + 2]环加成反应：多取代二氢萘醇的合成。

Sc(OTf) Catalyzed [4 + 2]-Annulation Reaction between Electron-Rich Phenols and Donor-Acceptor Cyclopropanes: Synthesis of Polysubstituted Dihydronaphthols.

机构信息

State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University , Lanzhou, Gansu P. R. China , 730000.

出版信息

J Org Chem. 2017 Jan 20;82(2):1013-1023. doi: 10.1021/acs.joc.6b02566. Epub 2017 Jan 9.

DOI:10.1021/acs.joc.6b02566

PMID:27997799

Abstract

On the basis of the Lewis acid-catalyzed Friedel-Crafts alkylation between 1-acyl-2-arylcyclopropanecarboxylate esters and electron-rich phenols, a Sc(OTf) catalyzed cascade [4 + 2]-annulation reaction was developed for the direct synthesis of polysubstituted dihydronaphthols from phenols. In this reaction, the structure of products is dominated by the directing effect of the substituent groups on phenols. Meanwhile, a one-pot Friedel-Crafts alkylation/oxidative cyclization reaction was also developed for the synthesis of spiro-fused 2,5-cyclohexadienones.

摘要

基于 1-酰基-2-芳基环丙羧酸酯和富电子苯酚之间的路易斯酸催化的傅-克烷基化反应，开发了一种 Sc(OTf) 催化的级联[4+2]-环加成反应，用于直接从苯酚合成多取代的二氢萘醇。在该反应中，产物的结构主要由酚上取代基的导向效应决定。同时，还开发了一种一锅傅-克烷基化/氧化环化反应，用于合成螺[2.5]环己二烯酮。