Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 88, Issue 11, Pages 7454-7462Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.3c00006
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The asymmetric addition of terminal alkynes catalyzed by a transition metal to isatins is an efficient and economical method for synthesizing 3-alkynyl-3-hydroxy-2-oxindoles. Using a new dimeric chiral quaternary ammonium derived from quinine as the cationic inducer, under mild conditions, the desired chiral compounds can be obtained in good to high yields with high enantioselectivity (<= 99% ee), and a variety of aryl-substituted terminal alkynes and substituted isatins are tolerated in this reaction.
Asymmetric addition of terminal alkynes catalyzed bya transitionmetal to isatins obviously is an efficient and economic method forthe synthesis of 3-alkynyl-3-hydroxy-2-oxindoles. The new dimericchiral quaternary ammoniums derived from a natural chiral alkaloid,quinine, can be used as cationic inducers of the enantioselectivityfor the Ag-(I)-catalyzed alkynylation of isatin derivatives under mildconditions. The desired chiral 3-alkynyl-3-hydroxy-2-oxindoles canbe obtained in good to high yields with high to excellent enantioselectivites(<= 99% ee). A variety of aryl-substituted terminal alkynes andsubstituted isatins are tolerated in this reaction.
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