Strategic enzymatic enantioselective desymmetrization of prochiral cyclohexa-2,5-dienones.
Chem Commun (Camb)
; 60(52): 6647-6650, 2024 Jun 25.
Article
in 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.
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Main subject:
Bacillus subtilis
Language:
En
Journal:
Chem Commun (Camb)
Journal subject:
QUIMICA
Year:
2024
Document type:
Article
Affiliation country:
India
Country of publication:
Reino Unido