Recyclable and Stable <i>α</i>-Methylproline-Derived Chiral Ligands for the Chemical Dynamic Kinetic Resolution of free <i>C,N</i>-Unprotected <i>α</i>-Amino Acids

Recyclable and Stable <i>α</i>-Methylproline-Derived Chiral Ligands for the Chemical Dynamic Kinetic Resolution of free <i>C,N</i>-Unprotected <i>α</i>-Amino Acids

A novel special designed, stable, and recyclable chiral ligand bearing a quaternary carbon was developed for chemical dynamic kinetic resolution (DKR) of free <i>C,N</i>-unprotected racemic &#945;-amino acids via Schiff base intermediates. This method furnishes high yields with excel...

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Main Authors: Shuangjie Shu, Liang Zhao, Shengbin Zhou, Chenglin Wu, Hong Liu, Jiang Wang
Format: Article
Language:English
Published: MDPI AG 2019-06-01
Series:Molecules
Subjects:
quaternary carbon
dynamic kinetic resolution
unprotected <i>α</i>-amino acids
Schiff base intermediates
ligands
Online Access:https://www.mdpi.com/1420-3049/24/12/2218
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spelling doaj-45362f332bb34fd79f346d621a519d442020-11-25T01:14:02ZengMDPI AGMolecules1420-30492019-06-012412221810.3390/molecules24122218molecules24122218Recyclable and Stable <i>α</i>-Methylproline-Derived Chiral Ligands for the Chemical Dynamic Kinetic Resolution of free <i>C,N</i>-Unprotected <i>α</i>-Amino AcidsShuangjie Shu0Liang Zhao1Shengbin Zhou2Chenglin Wu3Hong Liu4Jiang Wang5State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zu Chong Zhi Road, Shanghai 201203, ChinaState Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zu Chong Zhi Road, Shanghai 201203, ChinaState Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zu Chong Zhi Road, Shanghai 201203, ChinaState Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zu Chong Zhi Road, Shanghai 201203, ChinaState Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zu Chong Zhi Road, Shanghai 201203, ChinaState Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zu Chong Zhi Road, Shanghai 201203, ChinaA novel special designed, stable, and recyclable chiral ligand bearing a quaternary carbon was developed for chemical dynamic kinetic resolution (DKR) of free <i>C,N</i>-unprotected racemic &#945;-amino acids via Schiff base intermediates. This method furnishes high yields with excellent enantioselectivity, has a broad substrate scope, and uses operationally simple and convenient conditions. The present chemical DKR is a practical and useful method for the preparation of enantiopure &#945;-amino acids.https://www.mdpi.com/1420-3049/24/12/2218quaternary carbondynamic kinetic resolutionunprotected <i>α</i>-amino acidsSchiff base intermediatesligands
collection DOAJ
language English
format Article
sources DOAJ
author Shuangjie Shu
Liang Zhao
Shengbin Zhou
Chenglin Wu
Hong Liu
Jiang Wang
spellingShingle Shuangjie Shu
Liang Zhao
Shengbin Zhou
Chenglin Wu
Hong Liu
Jiang Wang
Recyclable and Stable <i>α</i>-Methylproline-Derived Chiral Ligands for the Chemical Dynamic Kinetic Resolution of free <i>C,N</i>-Unprotected <i>α</i>-Amino Acids
Molecules
quaternary carbon
dynamic kinetic resolution
unprotected <i>α</i>-amino acids
Schiff base intermediates
ligands
author_facet Shuangjie Shu
Liang Zhao
Shengbin Zhou
Chenglin Wu
Hong Liu
Jiang Wang
author_sort Shuangjie Shu
title Recyclable and Stable <i>α</i>-Methylproline-Derived Chiral Ligands for the Chemical Dynamic Kinetic Resolution of free <i>C,N</i>-Unprotected <i>α</i>-Amino Acids
title_short Recyclable and Stable <i>α</i>-Methylproline-Derived Chiral Ligands for the Chemical Dynamic Kinetic Resolution of free <i>C,N</i>-Unprotected <i>α</i>-Amino Acids
title_full Recyclable and Stable <i>α</i>-Methylproline-Derived Chiral Ligands for the Chemical Dynamic Kinetic Resolution of free <i>C,N</i>-Unprotected <i>α</i>-Amino Acids
title_fullStr Recyclable and Stable <i>α</i>-Methylproline-Derived Chiral Ligands for the Chemical Dynamic Kinetic Resolution of free <i>C,N</i>-Unprotected <i>α</i>-Amino Acids
title_full_unstemmed Recyclable and Stable <i>α</i>-Methylproline-Derived Chiral Ligands for the Chemical Dynamic Kinetic Resolution of free <i>C,N</i>-Unprotected <i>α</i>-Amino Acids
title_sort recyclable and stable <i>α</i>-methylproline-derived chiral ligands for the chemical dynamic kinetic resolution of free <i>c,n</i>-unprotected <i>α</i>-amino acids
publisher MDPI AG
series Molecules
issn 1420-3049
publishDate 2019-06-01
description A novel special designed, stable, and recyclable chiral ligand bearing a quaternary carbon was developed for chemical dynamic kinetic resolution (DKR) of free <i>C,N</i>-unprotected racemic &#945;-amino acids via Schiff base intermediates. This method furnishes high yields with excellent enantioselectivity, has a broad substrate scope, and uses operationally simple and convenient conditions. The present chemical DKR is a practical and useful method for the preparation of enantiopure &#945;-amino acids.
topic quaternary carbon
dynamic kinetic resolution
unprotected <i>α</i>-amino acids
Schiff base intermediates
ligands
url https://www.mdpi.com/1420-3049/24/12/2218
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AT liangzhao recyclableandstableiaimethylprolinederivedchiralligandsforthechemicaldynamickineticresolutionoffreeicniunprotectediaiaminoacids
AT shengbinzhou recyclableandstableiaimethylprolinederivedchiralligandsforthechemicaldynamickineticresolutionoffreeicniunprotectediaiaminoacids
AT chenglinwu recyclableandstableiaimethylprolinederivedchiralligandsforthechemicaldynamickineticresolutionoffreeicniunprotectediaiaminoacids
AT hongliu recyclableandstableiaimethylprolinederivedchiralligandsforthechemicaldynamickineticresolutionoffreeicniunprotectediaiaminoacids
AT jiangwang recyclableandstableiaimethylprolinederivedchiralligandsforthechemicaldynamickineticresolutionoffreeicniunprotectediaiaminoacids
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