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Biocatalytic asymmetric ring-opening of dihydroisoxazoles: a cyanide-free route to complementary enantiomers of β-hydroxy nitriles from olefins

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Abstract

By combination of the cyanide-free synthesis of chiral nitriles and the Kemp elimination reaction catalyzed by aldoxime dehydratases, we herein report a new application of aldoxime dehydratase in the asymmetric ring-opening of 5-sub-4,5-dihydroisoxazoles to synthesize chiral β-hydroxy nitriles with broad substrate scope, excellent enantioselectivity (up to 99% ee), and good turnover number (up to 11 s−1). Upon simple isolation and treatment with an alkaline reagent, the remaining chiral 5-sub-4,5-dihydroisoxazoles can be easily transformed into their corresponding β-hydroxy nitriles. Using site-directed mutagenesis, a ferrous Heme-containing active site was confirmed and two possible deprotonation pathways were proposed. To the best of our knowledge, this is the first enzymatic reaction used to construct a chiral hydroxyl group and nitrile group in one-step starting from a simple alkene, which provides a novel and useful strategy for the synthesis of complementary enantiomers of β-hydroxy nitriles.

Graphical abstract: Biocatalytic asymmetric ring-opening of dihydroisoxazoles: a cyanide-free route to complementary enantiomers of β-hydroxy nitriles from olefins

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Article information


Submitted
26 Apr 2020
Accepted
24 Jun 2020
First published
24 Jun 2020

This article is Open Access

Green Chem., 2020, Advance Article
Article type
Paper

Biocatalytic asymmetric ring-opening of dihydroisoxazoles: a cyanide-free route to complementary enantiomers of β-hydroxy nitriles from olefins

D. Zheng and Y. Asano, Green Chem., 2020, Advance Article , DOI: 10.1039/D0GC01445A

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