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

[Image: see text] 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 a...

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Autores principales: González-Rodríguez, Jorge, Albarrán-Velo, Jesús, Soengas, Raquel G., Lavandera, Iván, Gotor-Fernández, Vicente, Rodríguez-Solla, Humberto
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9552227/
https://www.ncbi.nlm.nih.gov/pubmed/36154101
http://dx.doi.org/10.1021/acs.orglett.2c02592
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author González-Rodríguez, Jorge
Albarrán-Velo, Jesús
Soengas, Raquel G.
Lavandera, Iván
Gotor-Fernández, Vicente
Rodríguez-Solla, Humberto
author_facet González-Rodríguez, Jorge
Albarrán-Velo, Jesús
Soengas, Raquel G.
Lavandera, Iván
Gotor-Fernández, Vicente
Rodríguez-Solla, Humberto
author_sort González-Rodríguez, Jorge
collection PubMed
description [Image: see text] 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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spelling pubmed-95522272022-10-12 Synthesis of Optically Active syn- and anti-Chlorohydrins through a Bienzymatic Reductive Cascade González-Rodríguez, Jorge Albarrán-Velo, Jesús Soengas, Raquel G. Lavandera, Iván Gotor-Fernández, Vicente Rodríguez-Solla, Humberto Org Lett [Image: see text] 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)). American Chemical Society 2022-09-26 2022-10-07 /pmc/articles/PMC9552227/ /pubmed/36154101 http://dx.doi.org/10.1021/acs.orglett.2c02592 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle González-Rodríguez, Jorge
Albarrán-Velo, Jesús
Soengas, Raquel G.
Lavandera, Iván
Gotor-Fernández, Vicente
Rodríguez-Solla, Humberto
Synthesis of Optically Active syn- and anti-Chlorohydrins through a Bienzymatic Reductive Cascade
title Synthesis of Optically Active syn- and anti-Chlorohydrins through a Bienzymatic Reductive Cascade
title_full Synthesis of Optically Active syn- and anti-Chlorohydrins through a Bienzymatic Reductive Cascade
title_fullStr Synthesis of Optically Active syn- and anti-Chlorohydrins through a Bienzymatic Reductive Cascade
title_full_unstemmed Synthesis of Optically Active syn- and anti-Chlorohydrins through a Bienzymatic Reductive Cascade
title_short Synthesis of Optically Active syn- and anti-Chlorohydrins through a Bienzymatic Reductive Cascade
title_sort synthesis of optically active syn- and anti-chlorohydrins through a bienzymatic reductive cascade
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9552227/
https://www.ncbi.nlm.nih.gov/pubmed/36154101
http://dx.doi.org/10.1021/acs.orglett.2c02592
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