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

doi:10.1021/acs.orglett.9b01556

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

Chemistry (Twin Cities)

Research output: Contribution to journal › Article › peer-review

26 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 language	English (US)
Pages (from-to)	4355-4358
Number of pages	4
Journal	Organic Letters
Volume	21
Issue number	11
DOIs	https://doi.org/10.1021/acs.orglett.9b01556
State	Published - 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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10.1021/acs.orglett.9b01556

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

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.",

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AU - Ott, Amy A.

AU - Liu, En Chih

AU - Topczewski, Joseph J.

N1 - 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.

PY - 2019/6/7

Y1 - 2019/6/7

N2 - 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.

AB - 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.

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

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