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

Kui Liao
, Yi Gong
, Ren Yi Zhu
, Cai Wang
, Feng Zhou^*
, Jian Zhou^*

^*Corresponding author for this work

School of Chemistry and Molecular Engineering

East China Normal University
CAS - Shanghai Institute of Organic Chemistry

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

58 Scopus citations

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.

Original language	English
Pages (from-to)	8488-8493
Number of pages	6
Journal	Angewandte Chemie - International Edition
Volume	60
Issue number	15
DOIs	https://doi.org/10.1002/anie.202016286
State	Published - 6 Apr 2021

Keywords

CuAAC
PYBOX-phosphonate ligands
kinetic resolution
multifunctional tertiary alcohols

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10.1002/anie.202016286

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title = "Highly Enantioselective CuAAC of Functional Tertiary Alcohols Featuring an Ethynyl Group and Their Kinetic Resolution",

abstract = "The first highly enantioselective CuI-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",

author = "Kui Liao and Yi Gong and Zhu, \{Ren Yi\} and Cai Wang and Feng Zhou and Jian Zhou",

note = "Publisher Copyright: {\textcopyright} 2020 Wiley-VCH GmbH",

year = "2021",

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doi = "10.1002/anie.202016286",

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T1 - Highly Enantioselective CuAAC of Functional Tertiary Alcohols Featuring an Ethynyl Group and Their Kinetic Resolution

AU - Liao, Kui

AU - Gong, Yi

AU - Zhu, Ren Yi

AU - Wang, Cai

AU - Zhou, Feng

AU - Zhou, Jian

PY - 2021/4/6

Y1 - 2021/4/6

N2 - The first highly enantioselective CuI-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.

AB - The first highly enantioselective CuI-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.

KW - CuAAC

KW - PYBOX-phosphonate ligands

KW - kinetic resolution

KW - multifunctional tertiary alcohols

UR - https://www.scopus.com/pages/publications/85101814819

U2 - 10.1002/anie.202016286

DO - 10.1002/anie.202016286

M3 - 文章

C2 - 33369828

AN - SCOPUS:85101814819

SN - 1433-7851

VL - 60

SP - 8488

EP - 8493

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 15

ER -

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

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Keywords

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