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Regio- and stereoselective multi-enzymatic aminohydroxylation of ?-methylstyrene using dioxygen, ammonia and formate.

ABSTRACT: We report an enzymatic route for the formal regio- and stereoselective aminohydroxylation of ?-methylstyrene that consumes only dioxygen, ammonia and formate; carbonate is the by-product. The biocascade entails highly selective epoxidation, hydrolysis and hydrogen-borrowing alcohol amination. Thus, ?-methylstyrene was converted into 1R,2R and 1S,2R-phenylpropanolamine in 59-63% isolated yields, and up to >99.5: <0.5 dr and er.

SUBMITTER: Corrado ML

PROVIDER: S-EPMC7116804 | biostudies-literature | 2019 Dec

REPOSITORIES: biostudies-literature

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Regio- and stereoselective multi-enzymatic aminohydroxylation of β-methylstyrene using dioxygen, ammonia and formate.

Corrado Maria L ML Knaus Tanja T Mutti Francesco G FG

Green chemistry : an international journal and green chemistry resource : GC 20191029 23

We report an enzymatic route for the formal regio- and stereoselective aminohydroxylation of β-methylstyrene that consumes only dioxygen, ammonia and formate; carbonate is the by-product. The biocascade entails highly selective epoxidation, hydrolysis and hydrogen-borrowing alcohol amination. Thus, β-methylstyrene was converted into 1R,2R and 1S,2R-phenylpropanolamine in 59-63% isolated yields, and up to >99.5: <0.5 dr and er. ...[more]

PMID: 33628112

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