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Brønsted acid-catalysed intramolecular ring opening of 2-(aryloxymethyl)-3-aryloxiranes leading to trans-4-arylchroman-3-ols: scope and limitations†
Runjun Devi,Tapasi Kalita,Sajal Kumar Das
RSC Advances Pub Date : 04/20/2015 00:00:00 , DOI:10.1039/C5RA02193F
Abstract

An operationally simple and metal-free method for the synthesis of a series of trans-4-arylchroman-3-ols via Brønsted acid (TsOH·H2O) catalysed stereoselective intramolecular Friedel–Crafts alkylation of electron-rich arenes by tethered epoxides is developed. The reactions neither need strict anhydrous conditions nor suffer from the use of expensive Lewis/Brønsted acids.

Graphical abstract: Brønsted acid-catalysed intramolecular ring opening of 2-(aryloxymethyl)-3-aryloxiranes leading to trans-4-arylchroman-3-ols: scope and limitations
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