Synlett

Highly efficient synthesis of multisubstituted 2-acyl furans via PIFA/I2-mediated oxidative cycloisomerization of cis-2-En-4-yn-1-ols

X Du, H Chen, Y Chen, J Chen, Y Liu

Index: Du, Xiangwei; Chen, Haoyi; Chen, Yifeng; Chen, Jingjin; Liu, Yuanhong Synlett, 2011 , # 7 p. 1010 - 1014

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Citation Number: 11

Abstract

Abstract A novel oxidative cycloisomerization of cis-enynols has been developed using a combination of hypervalent iodine (III) reagent, molecular iodine, and a base. This method offers an efficient synthesis of 2-acyl furans with diverse substitution patterns in a regioselective manner under mild reaction conditions. A mechanistic proposal for these transformations involving alkyne activation by trifluoroacetylhypoiodite generated in situ is ...