Expeditious preparation of β- sec -alkyl vicinal amino alcohols used for chiral ligand synthesis

An economical route providing quick access to chiral β-amino alcohols bearing one β- sec -alkyl group was developed. This protocol starts with commercially available and cheap chiral sources such as derivatives of l -serine and l -threonine. A series of vicinal amino alcohols with high optical purit...

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Bibliographic Details
Published inOrganic & biomolecular chemistry Vol. 21; no. 30; pp. 6111 - 6114
Main Authors Huang, Guoqi, Wu, Yu, Gong, Hegui, Chen, Yunrong
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 02.08.2023
Royal Society of Chemistry
Subjects
Alcohols
Chemistry
Chemistry, Organic
L-Serine
Physical Sciences
Science & Technology
Steric hindrance
Synthesis
Threonine
CATALYSIS
POTENT
NICKEL
PHOTOREDOX
ACIDS
ARYLATION
ISOMERIZATION
ASYMMETRIC HYDROGENATION
DERIVATIVES
ALLYLAMINES
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Summary:An economical route providing quick access to chiral β-amino alcohols bearing one β- sec -alkyl group was developed. This protocol starts with commercially available and cheap chiral sources such as derivatives of l -serine and l -threonine. A series of vicinal amino alcohols with high optical purity were prepared in good yields through 4 or 6 operationally simple steps. Two different strategies (three routes) were designed for the synthesis of amino alcohols bearing β- sec -alkyl groups with various steric hindrance.
Bibliography:ObjectType-Article-1
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ISSN:1477-0520
1477-0539
1477-0539
DOI:10.1039/D3OB00803G