Asymmetric carbohydroxylation of alkenes via sequential photocatalytic oxo-alkylation and enzymatic reduction

Yiyin Liu; Kun Zhu; Xuemei Li; Xiaoyun Wu; Jinhui Feng; Atefeh Roosta; Qiaqing Wu; Dunming Zhu

Tetrahedron Chem (Aug 2024)

Asymmetric carbohydroxylation of alkenes via sequential photocatalytic oxo-alkylation and enzymatic reduction

Yiyin Liu,
Kun Zhu,
Xuemei Li,
Xiaoyun Wu,
Jinhui Feng,
Atefeh Roosta,
Qiaqing Wu,
Dunming Zhu

Affiliations

Yiyin Liu: National Engineering Research Center of Industrial Enzymes and Tianjin Engineering Research Center of Biocatalytic Technology, Tianjin Institute of Industrial Biotechnology, Chinese Academy of Sciences. National Technology Innovation Center for Synthetic Biology, Tianjin, 300308, China
Kun Zhu: National Engineering Research Center of Industrial Enzymes and Tianjin Engineering Research Center of Biocatalytic Technology, Tianjin Institute of Industrial Biotechnology, Chinese Academy of Sciences. National Technology Innovation Center for Synthetic Biology, Tianjin, 300308, China
Xuemei Li: National Engineering Research Center of Industrial Enzymes and Tianjin Engineering Research Center of Biocatalytic Technology, Tianjin Institute of Industrial Biotechnology, Chinese Academy of Sciences. National Technology Innovation Center for Synthetic Biology, Tianjin, 300308, China
Xiaoyun Wu: National Engineering Research Center of Industrial Enzymes and Tianjin Engineering Research Center of Biocatalytic Technology, Tianjin Institute of Industrial Biotechnology, Chinese Academy of Sciences. National Technology Innovation Center for Synthetic Biology, Tianjin, 300308, China; Key Laboratory of Industrial Fermentation Microbiology, Ministry of Education, College of Biotechnology, Tianjin University of Science & Technology, Tianjin, 300457, China
Jinhui Feng: National Engineering Research Center of Industrial Enzymes and Tianjin Engineering Research Center of Biocatalytic Technology, Tianjin Institute of Industrial Biotechnology, Chinese Academy of Sciences. National Technology Innovation Center for Synthetic Biology, Tianjin, 300308, China
Atefeh Roosta: National Engineering Research Center of Industrial Enzymes and Tianjin Engineering Research Center of Biocatalytic Technology, Tianjin Institute of Industrial Biotechnology, Chinese Academy of Sciences. National Technology Innovation Center for Synthetic Biology, Tianjin, 300308, China
Qiaqing Wu: National Engineering Research Center of Industrial Enzymes and Tianjin Engineering Research Center of Biocatalytic Technology, Tianjin Institute of Industrial Biotechnology, Chinese Academy of Sciences. National Technology Innovation Center for Synthetic Biology, Tianjin, 300308, China; Corresponding author.
Dunming Zhu: National Engineering Research Center of Industrial Enzymes and Tianjin Engineering Research Center of Biocatalytic Technology, Tianjin Institute of Industrial Biotechnology, Chinese Academy of Sciences. National Technology Innovation Center for Synthetic Biology, Tianjin, 300308, China; Corresponding author.

Journal volume & issue: Vol. 11
p. 100083

Abstract

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Asymmetric carbohydroxylation of alkenes offers an efficient approach to access chiral alcohols, a class of versatile building blocks in pharmaceutical and agrochemical industries, from abundant simple alkenes. Herein we reported a sequential photo-biocatalysis protocol for the asymmetric carbohydroxylation of alkenes, involving a stepwise photocatalytic decarboxylative radical addition/Kornblum oxidation and enzymatic reduction. A series of chiral alcohols with bulky structures were synthesized in up to 75 % isolated yields and 99 % ee from N-hydroxyphthalimide esters and aryl alkenes.

Published in Tetrahedron Chem

ISSN: 2666-951X (Online)
Publisher: Elsevier
Country of publisher: United Kingdom
LCC subjects: Science: Chemistry: Organic chemistry
Website: https://www.journals.elsevier.com/tetrahedron-chem

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