Abstract
We report the development of a modular, one-pot, sequential chemoenzymatic system for the formal enantioselective construction of the C–C bond in 2-aryl 1,4-dicarbonyl compounds. This sequence comprises a rhodium-catalyzed diazocoupling that provides >9:1 selectivity for heterocoupling of two diazoesters and a reduction mediated by an ene-reductase (ER), which occurs in up to 99% enantiomeric excess (ee). The high yield and enantioselectivity of this system result from the preferential generation of an (E)-alkene from the diazo coupling reaction and selective reduction of the (E)-alkene in a mixture of (E) and (Z) isomers by the ER. Screening of a panel of ERs revealed that OPR1 from Lycopersicum esculentum catalyzes the reduction of bulky tert-butyl or benzyl esters to afford chiral diesters that are poised for orthogonal reactions at the two distinct ester units of the product. Overall, this work demonstrates the benefit of combining organometallic and enzymatic catalysis to create unusual overall trans...
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Disclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.