Highly Enantioselective CuAAC of Functional Tertiary Alcohols Featuring an Ethynyl Group and Their Kinetic Resolution

Kui Liao; Yi Gong; Ren-Yi Zhu; Cai Wang; Feng Zhou; Jian Zhou

doi:10.1002/anie.202016286

Highly Enantioselective CuAAC of Functional Tertiary Alcohols Featuring an Ethynyl Group and Their Kinetic Resolution

Angew Chem Int Ed Engl. 2021 Apr 6;60(15):8488-8493. doi: 10.1002/anie.202016286. Epub 2021 Mar 1.

Authors

Kui Liao¹, Yi Gong¹, Ren-Yi Zhu¹, Cai Wang¹, Feng Zhou¹, Jian Zhou^{1

2}

Affiliations

¹ Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, 3663N Zhongshan Road, Shanghai, 200062, China.
² State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, 200032, P. R. China.

PMID: 33369828
DOI: 10.1002/anie.202016286

Abstract

The first highly enantioselective Cu^I -catalyzed azide-alkyne cycloaddition (CuAAC) of tertiary alcohols and their kinetic resolution is reported. This approach allows facile access to multifunctional tertiary alcohols featuring an α-ethynyl or α-triazole moiety, and represents the first successful kinetic resolution of racemates with a tetrasubstituted carbon stereocenter via CuAAC. Newly developed pyridinebisoxazoline (PYBOX) ligands with a C4 phosphonate group play a key role.

Keywords: CuAAC; PYBOX-phosphonate ligands; kinetic resolution; multifunctional tertiary alcohols.

Abstract

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