Design and Application of m-Hydroxybenzyl Alcohols in Regioselective(3+3)Cycloadditions of 2-Indolymethanols  

作　　者：Yi-Cheng Shi Xin-Yu Yan Ping Wu Song Jiang Ran Xu Wei Tan Feng Shi 

机构地区：[1]Research Center of Chiral Functional Heterocycles,School of Chemistry and Materials Science,Jiangsu Normal University,Xuzhou,Jiangsu 221116,China [2]School of Petrochemical Engineering,Changzhou University,Changzhou,Jiangsu 213164,China

出　　处：《Chinese Journal of Chemistry》2023年第1期27-36,共10页中国化学（英文版）

基　　金：financial support from the National Natural Science Foundation of China(22125104 and 21831007);the Natural Science Foundation of Jiangsu Province(BK20210916);the High Education Natural Science Foundation of Jiangsu Province(No.21KJB150009);Undergraduate Students Project of Jiangsu Province(No.202110320019Z).

摘　　要：A new class of m-hydroxybenzyl alcohols has been designed as competent three-carbon building blocks and achieved their applica-tion in 2-indolylmethanol-involved regioselective(3+3)cycloadditions under the catalysis of Br?nsted acids.By this appoach,a series of indole-fused six-membered cycloadducts have been synthesized in overall good yields(up to 98%)with excellent regioselectivity(all>95:5 rr),thus affording a powerful method for the construction of indole-fused six-membered rings.Moreover,a catalytic asymmetric version of this(3+3)cycloaddition has been preliminarily investigated,which revealed the potential of the reaction for constructing chiral indole-fused six-membered rings in an enantioselective manner.This work not only has accomplished the first design of m-hydroxybenzyl alcohols as competent reactants,but also represents the first application of m-hydroxybenzyl alcohols as three-carbon building blocks in cycloadditions.In addition,this work provides a good example for regioselective and C3-nucleophilic(3+3)cycloadditions of 2-indolylmethanols,which will substantially enrich the chemistry of 2-indolylmethanols.

关 键 词：m-Hydroxybenzyl alcohols 2-lndolymethanols CYCLOADDITION Regioselectivity HETEROCYCLES 

分 类 号：O62[理学—有机化学]