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Enantioselective Cu(I)-Catalyzed Cycloaddition of Prochiral Diazides with Terminal or 1-Iodoalkynes

Cai Wang, Ren‐Yi Zhu, Kui Liao, Feng Zhou, Jian Zhou

2020Organic Letters38 citationsDOI

Abstract

We report an unprecedented highly enantioselective desymmetric Cu(I)-catalyzed 1,3-dipolar cycloaddition of diazides with terminal alkynes and 1-iodoalkynes, affording tertiary alcohols bearing a 1,2,3-triazole moiety in high yield and excellent ee value. PYBOX ligands with a C4 shielding group once again show the promising ability to achieve higher enantioselectivity.

Topics & Concepts

ChemistryCycloadditionEnantioselective synthesisMoietyTertiary alcoholsCatalysisYield (engineering)Terminal (telecommunication)Organic chemistryComputer scienceTelecommunicationsMaterials scienceMetallurgyClick Chemistry and ApplicationsCyclopropane Reaction MechanismsSynthesis and Catalytic Reactions
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