Strategic enzymatic enantioselective desymmetrization of prochiral cyclohexa-2,5-dienones.
Chem Commun (Camb)
; 60(52): 6647-6650, 2024 Jun 25.
Article
em En
| MEDLINE
| ID: mdl-38856301
ABSTRACT
Asymmetric desymmetrization through the selective reduction of one double bond of prochiral 2,5-cyclohexadienones is highly challenging. A novel method has been developed for synthesizing chiral cyclohexenones by employing an ene-reductase (Bacillus subtilis YqjM) enzyme that belongs to the OYE family. Our strategy demonstrates high substrate scope and enantioselectivity towards substrates containing all-carbon as well as heteroatom (O, N)-containing quaternary centers. The mechanistic studies (kH/D = â¼1.8) indicate that hydride transfer is probably the rate-limiting step. Mutation of several active site residues did not affect the stereochemical outcomes. This work provides a convenient way of synthesizing various enantioselective γ,γ-disubstituted cyclohexanones using enzymes.
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1
Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Bacillus subtilis
Idioma:
En
Ano de publicação:
2024
Tipo de documento:
Article