Literature DB >> 31117717

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

Juliana R Alexander1, Amy A Ott1, En-Chih Liu1, Joseph J Topczewski1.   

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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Year:  2019        PMID： 31117717      PMCID： PMC6631410          DOI： 10.1021/acs.orglett.9b01556

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  23 in total

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2.  Enantioselective Nickel-Catalyzed Alkyne-Azide Cycloaddition by Dynamic Kinetic Resolution.

Authors:  En-Chih Liu; Joseph J Topczewski
Journal:  J Am Chem Soc       Date:  2021-04-02       Impact factor: 15.419

3.  Coetaneous catalytic kinetic resolution of alkynes and azides through asymmetric triazole formation.

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6.  Kinetic resolution of cyclic benzylic azides enabled by site- and enantioselective C(sp3)-H oxidation.

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