Kinetic Resolution of Cyclic Secondary Azides, Using an Enantioselective Copper-Catalyzed Azide-Alkyne Cycloaddition

Juliana R. Alexander, Amy A. Ott, En Chih Liu, Joseph J. Topczewski

Research output: Contribution to journalArticlepeer-review

10 Scopus citations

Abstract

An enantioselective copper-catalyzed azide-alkyne cycloaddition (E-CuAAC) is reported by kinetic resolution. Chiral triazoles were isolated in high yield with limiting alkyne (up to 97:3 enantiomeric ratio (er)). A range of substrates were tolerated (>30 examples), and the reaction was scaled to >1 g. The er of a triazole product could be enhanced by recrystallization and the recovered scalemic azide could be racemized and recycled. Recycling the azide allows efficient use of the undesired azide enantiomer.

Original languageEnglish (US)
Pages (from-to)4355-4358
Number of pages4
JournalOrganic Letters
Volume21
Issue number11
DOIs
StatePublished - Jun 7 2019

Bibliographical note

Funding Information:
This research was supported by the National Institute of General Medical Sciences of the National Institutes of Health, under Award No. R35GM124718. We also acknowledge NIH Shared Instrumentation Grant No. S10OD011952.

Publisher Copyright:
© 2019 American Chemical Society.

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