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Literature DB >> 33369828

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

Kui Liao¹, Yi Gong¹, Ren-Yi Zhu¹, Cai Wang¹, Feng Zhou¹, Jian Zhou^1,2.

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.

Entities: Chemical

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

Year: 2021 PMID： 33369828 DOI： 10.1002/anie.202016286

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

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Cited

3 in total

1. Organocatalytic enantioselective S_N1-type dehydrative nucleophilic substitution: access to bis(indolyl)methanes bearing quaternary carbon stereocenters.

Authors: Wen-Run Zhu; Qiong Su; Xiao-Yi Deng; Jia-Sheng Liu; Tao Zhong; Shan-Shui Meng; Ji-Tao Yi; Jiang Weng; Gui Lu
Journal: Chem Sci Date: 2021-11-23 Impact factor: 9.969

2. Nonlinear Optical and Ion Sensor Properties of Novel Molecules Conjugated by Click Chemistry.

Authors: Zongcheng Miao; Yaqin Chu; Lei Wang; Wenqing Zhu; Dong Wang
Journal: Polymers (Basel) Date: 2022-04-08 Impact factor: 4.967

3. Gene mining, codon optimization and analysis of binding mechanism of an aldo-keto reductase with high activity, better substrate specificity and excellent solvent tolerance.

Authors: Wei Jiang; Xiaoli Fu; Weiliang Wu
Journal: PLoS One Date: 2021-12-02 Impact factor: 3.240

3 in total

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

1. Organocatalytic enantioselective SN1-type dehydrative nucleophilic substitution: access to bis(indolyl)methanes bearing quaternary carbon stereocenters.

2. Nonlinear Optical and Ion Sensor Properties of Novel Molecules Conjugated by Click Chemistry.

3. Gene mining, codon optimization and analysis of binding mechanism of an aldo-keto reductase with high activity, better substrate specificity and excellent solvent tolerance.

1. Organocatalytic enantioselective S_N1-type dehydrative nucleophilic substitution: access to bis(indolyl)methanes bearing quaternary carbon stereocenters.