A Versatile Entry to 3-Unsubstituted 2-Isoxazolines

Pohjakallio, Antti; Pihko, Petri M.

doi:10.1055/s-2008-1042900

Synlett

2008

DOI: 10.1055/s-2008-1042900

|View full text |Cite

A Versatile Entry to 3-Unsubstituted 2-Isoxazolines

Antti Pohjakallio¹,

Petri M. Pihko²

Abstract: A new catalytic method for the preparation of 3-unsubstituted 2-isoxazolines is reported. The isoxazolines are easily prepared from the aliphatic a,b-unsaturated aldehydes and simple oximes in the presence of an anilinium salt catalyst.

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...

Citation Types

Supporting

Mentioning

Contrasting

Year Published

2008

2021

Publication Types

Select...

Article2

Relationship

Self Cite0

Independent2

Authors

Journals

Cited by 2 publications

References 4 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

A Cyanide‐free Biocatalytic Process for Synthesis of Complementary Enantiomers of 4‐Chloro‐3‐hydroxybutanenitrile From Allyl Chloride

Zheng

Asano

2021

ChemCatChem

View full text Add to dashboard Cite

A biocatalyst used for selective ring scission of (±)‐5‐(chloromethyl)‐4, 5‐dihydroisoxazole to synthesize chiral (R)‐4‐chloro‐3‐hydroxybutanenitrile (90 % ee, 39 % isolated yield) and (S)‐5‐(chloromethyl)‐4, 5‐dihydroisoxazole (99 % ee, 39 % isolated yield) was developed by site‐saturated mutagenesis on aldoxime dehydratase derived from Pseudomonas chlororaphis B23 (OxdA). The positive mutant (OxdA‐L318I, E=68) improved the enantiomeric ratio E by 6‐fold as compared to the wild type enzyme (OxdA‐wild, E=11). The racemic precursor of (±)‐5‐(chloromethyl)‐4, 5‐dihydroisoxazole, used in the reaction, can be synthesized from readily available allyl chloride without utilizing highly toxic cyanide. The enantiopure (S)‐5‐(chloromethyl)‐4, 5‐dihydroisoxazole remaining in the kinetic resolution can be transformed into corresponding chiral (S)‐4‐chloro‐3‐hydroxybutanenitrile without loss of enantiomeric excess by treating it with triethylamine in acetonitrile (99 % ee, 72 % isolated yield) or catalysis of OxdA‐wild enzyme (99 % ee, 88 % isolated yield).

show abstract

A Cyanide‐free Biocatalytic Process for Synthesis of Complementary Enantiomers of 4‐Chloro‐3‐hydroxybutanenitrile From Allyl Chloride

Zheng

Asano

2021

ChemCatChem

View full text Add to dashboard Cite

show abstract

ChemInform Abstract: A Versatile Entry to 3‐Unsubstituted 2‐Isoxazolines.

Pohjakallio¹,

Pihko²

2008

ChemInform

View full text Add to dashboard Cite

show abstract

scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.

Contact Info

hi@scite.ai

10624 S. Eastern Ave., Ste. A-614

Henderson, NV 89052, USA

Blog Terms and Conditions API Terms Privacy Policy Contact Cookie Preferences Do Not Sell or Share My Personal Information

Made with 💙 for researchers

Part of the Research Solutions Family.

A Versatile Entry to 3-Unsubstituted 2-Isoxazolines

Abstract: A new catalytic method for the preparation of 3-unsubstituted 2-isoxazolines is reported. The isoxazolines are easily prepared from the aliphatic a,b-unsaturated aldehydes and simple oximes in the presence of an anilinium salt catalyst.

Cited by 2 publications

References 4 publications

A Cyanide‐free Biocatalytic Process for Synthesis of Complementary Enantiomers of 4‐Chloro‐3‐hydroxybutanenitrile From Allyl Chloride

A Cyanide‐free Biocatalytic Process for Synthesis of Complementary Enantiomers of 4‐Chloro‐3‐hydroxybutanenitrile From Allyl Chloride

ChemInform Abstract: A Versatile Entry to 3‐Unsubstituted 2‐Isoxazolines.

Contact Info

Product

Resources

About