A novel asymmetric[4+2]cycloaddition of indolylmethanols with aurones via chiral phosphoric acid(CPA)catalysis has been established.Enantioenriched indole-fused spiro compounds were obtained in good yields(60%-89%)wit...A novel asymmetric[4+2]cycloaddition of indolylmethanols with aurones via chiral phosphoric acid(CPA)catalysis has been established.Enantioenriched indole-fused spiro compounds were obtained in good yields(60%-89%)with excellent diastereoselectivities(up to>19:1 dr)and enantioselectivities(83%-99%ee)with broad substrate scope.This approach not only enabled the first catalytic asymmetric[4+2]cycloaddition of 3-methyl-2-indolylmethanols,but also represented different reactivity from traditional indolylmethanol chemistry.In this reaction,3-methyl-2-indolylmethanols behaved as C4 synthons rather than C3 synthons.展开更多
A highly efficient base-mediated diastereoselective[4+1]cycloaddition of ortho-tosylaminophenyl-substituted p-QMs with 3-chlorooxindoles has been developed to afford 3,2’-pyrrolidinyl spirooxindoles in high yields wi...A highly efficient base-mediated diastereoselective[4+1]cycloaddition of ortho-tosylaminophenyl-substituted p-QMs with 3-chlorooxindoles has been developed to afford 3,2’-pyrrolidinyl spirooxindoles in high yields with high diastereoselectivity through a domino 1,6-addition/cyclization sequence.This reaction exhibits broad substrate scope and excellent functional group tolerance.展开更多
基金the Qingdao Marine Science and Technology Center(No.2022QNLM030003-2)the Fundamental Research Funds for the Central Universities,Taishan Scholar Program of Shandong Province(No.tsqn202103152)+2 种基金National Natural Science Foundation of China(Nos.22201270,22471250)Natural Science Foundation of Shandong Province(No.ZR2021QB033)the National Key Research and Development Program of China(No.2022YFC2804400)for financial support.
文摘A novel asymmetric[4+2]cycloaddition of indolylmethanols with aurones via chiral phosphoric acid(CPA)catalysis has been established.Enantioenriched indole-fused spiro compounds were obtained in good yields(60%-89%)with excellent diastereoselectivities(up to>19:1 dr)and enantioselectivities(83%-99%ee)with broad substrate scope.This approach not only enabled the first catalytic asymmetric[4+2]cycloaddition of 3-methyl-2-indolylmethanols,but also represented different reactivity from traditional indolylmethanol chemistry.In this reaction,3-methyl-2-indolylmethanols behaved as C4 synthons rather than C3 synthons.
基金We are thankful for financial support from OUC,QNLM(LMDBCXRC201902,LMDBCXRC201903),tsqn201909056,tsqn202103152.The project is supported by the Fundamental Research Funds for the Central Universities.
文摘A highly efficient base-mediated diastereoselective[4+1]cycloaddition of ortho-tosylaminophenyl-substituted p-QMs with 3-chlorooxindoles has been developed to afford 3,2’-pyrrolidinyl spirooxindoles in high yields with high diastereoselectivity through a domino 1,6-addition/cyclization sequence.This reaction exhibits broad substrate scope and excellent functional group tolerance.
