Brønsted Acid-Catalyzed Cycloisomerization of But-2-yne-1, 4-diols with or without 1, 3-Dicarbonyl Compounds to Tri-and Tetrasubstituted Furans

SR Mothe, SJL Lauw, P Kothandaraman…

Index: Mothe, Srinivasa Reddy; Lauw, Sherman Jun Liang; Kothandaraman, Prasath; Chan, Philip Wai Hong Journal of Organic Chemistry, 2012 , vol. 77, # 16 p. 6937 - 6947

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Citation Number: 26

Abstract

A Brønsted acid-catalyzed method to prepare tri-and tetrasubstituted furans efficiently from cycloisomerization of but-2-yne-1, 4-diols with or without 1, 3-dicarbonyl compounds is described. By taking advantage of the orthogonal modes of reactivity of the alcoholic substrate through slight modification of the reaction conditions, a divergence in product selectivity was observed. At room temperature, p-TsOH· H2O-mediated tandem alkylation/ ...