Simplified Modular Access to Enantiopure 1,2-Aminoalcohols via Ni- Electrocatalytic Decarboxylative Arylation

Chiral aminoalcohols are omnipresent in bioactive compounds. Conventional strategies to access this motif involve multiple-step reactions to install requisite functionalities stere- oselectively using conventional polar bond analysis. This study re- veals that a simple chiral oxazolidine-based carbo...

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Published inChemRxiv
Main Authors Sun, Jiawei, Endo, Hirofumi, Emmanuel, Megan, Oderinde, Martins, Kawamata, Yu, baran, phil
Format Paper
LanguageEnglish
Published Washington American Chemical Society 14.12.2023
Edition1
Subjects
Carboxylic acids
Chemistry
Functional groups
Organic Chemistry
Organic Synthesis and Reactions
Oxazolidine
Electrochemistry
Cross-Coupling
Nickel
Aminoalcohols
Stereoselective
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Abstract Chiral aminoalcohols are omnipresent in bioactive compounds. Conventional strategies to access this motif involve multiple-step reactions to install requisite functionalities stere- oselectively using conventional polar bond analysis. This study re- veals that a simple chiral oxazolidine-based carboxylic acid can be readily transformed to substituted chiral aminoalcohols with high stereochemical control by Ni-electrocatalytic decarboxylative ary- lation. This general, robust and scalable coupling can be used to synthesize variety of medicinally important compounds, avoiding protecting and functional group manipulations thereby dramati- cally simplifying their preparation.
AbstractList Chiral aminoalcohols are omnipresent in bioactive compounds. Conventional strategies to access this motif involve multiple-step reactions to install requisite functionalities stere- oselectively using conventional polar bond analysis. This study re- veals that a simple chiral oxazolidine-based carboxylic acid can be readily transformed to substituted chiral aminoalcohols with high stereochemical control by Ni-electrocatalytic decarboxylative ary- lation. This general, robust and scalable coupling can be used to synthesize variety of medicinally important compounds, avoiding protecting and functional group manipulations thereby dramati- cally simplifying their preparation.
Author baran, phil
Oderinde, Martins
Sun, Jiawei
Endo, Hirofumi
Emmanuel, Megan
Kawamata, Yu
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Cross-Coupling
Nickel
Aminoalcohols
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Chemistry
Functional groups
Organic Chemistry
Organic Synthesis and Reactions
Oxazolidine
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Title Simplified Modular Access to Enantiopure 1,2-Aminoalcohols via Ni- Electrocatalytic Decarboxylative Arylation
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