Synthesis of Optically Active syn- and anti-Chlorohydrins through a Bienzymatic Reductive Cascade | Zendy

Jorge González-Rodríguez | Zendy; Jesús AlbarránVelo | Zendy; Raquel G. Soengas | Zendy; Iván Lavandera | Zendy; Vicente GotorFernández | Zendy; Humberto RodríguezSolla | Zendy

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Synthesis of Optically Active syn- and anti-Chlorohydrins through a Bienzymatic Reductive Cascade

Author(s) -

Jorge González-Rodríguez,

Jesús AlbarránVelo,

Raquel G. Soengas,

Iván Lavandera,

Vicente GotorFernández,

Humberto RodríguezSolla

Publication year - 2022

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.2c02592

Subject(s) - enantiopure drug , chemistry , diastereomer , optically active , isomerization , alcohol , enantiomer , enantiomeric excess , aldehyde , cascade , catalysis , organic chemistry , enantioselective synthesis , chromatography

A bienzymatic cascade has been designed and optimized to obtain enantiopure chlorohydrins starting from the corresponding 1-aryl-2-chlorobut-2-en-1-ones. For the synthesis of these α-chloroenones, a two-step sequence was developed consisting of the allylation of the corresponding aldehyde with 3-dichloroprop-1-ene, followed by oxidation and further isomerization. The selective cooperative catalytic system involving ene-reductases (EREDs) and alcohol dehydrogenases (ADHs) afforded the desired optically active chlorohydrins under mild reaction conditions in excellent conversions (up to >99%) and selectivities (up to >99:1 diastereomeric ratio (dr), >99% enantiomeric excess ( ee )).

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