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Enantioselective Carbonylative Cyclization of Alkenes with C-H Bonds for Synthesis of γ-Lactams Bearing an α-Quaternary Carbon.
J Am Chem Soc
January 2025
State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Frontiers Science Center for New Organic Matter, Tianjin 300071, China.
The development of effective synthetic methods to construct γ-lactams bearing a chiral α-quaternary carbon from relatively inert C(O)-H bonds with alkenes has been an elusive challenge. Herein, we used a naphthylamine-derived phosphine oxide ligating Ni and Al bimetallic catalyst to realize a carbonylative cyclization of formyl C-H bonds with alkenes, highly regio- and enantioselectively constructing γ-lactams bearing a chiral α-quaternary carbon in up to 99% yield and 98% ee. These γ-lactams proved to be versatile synthetic precursors for many biologically active molecules.
View Article and Find Full Text PDFCoimmobilized Dual Enzymes in a Continuous Flow Reactor for the Efficient Synthesis of Optically Pure γ/δ-Lactones.
ACS Appl Mater Interfaces
January 2025
State Key Laboratory of Bioreactor Engineering, Shanghai Collaborative Innovation Center for Biomanufacturing, East China University of Science and Technology, Shanghai 200237, China.
Enzyme catalysis is a promising method for producing chiral chemicals with high stereoselectivity under mild conditions. However, the traditional batch reaction suffers from low enzyme stability, low cofactor recycling, and poor enzyme reusability. Here, we present a continuous-flow method using coimmobilized dual enzymes for the synthesis of chiral γ-/δ-lactones, which are widely used in fragrances and flavors.
View Article and Find Full Text PDFSynthesis of γ-Amino Amides by Iridium-Catalyzed Enantioselective Hydroamination of Internal Alkenes Directed by an Amide.
Angew Chem Int Ed Engl
December 2024
Center of Basic Molecular Science (CBMS), Department of Chemistry, Tsinghua University, Beijing, 100084, China.
Catalytic regio- and enantioselective hydroamination of less activated internal alkenes presents a challenge to synthetic chemists due to their low reactivity and the difficulty in simultaneously controlling regio- and enantioselectivities. Here, we report an iridium-catalyzed enantioselective hydroamination of internal alkenes directed by an amide. The amide group on the alkene effectively directs the catalyst to overcome the low reactivity and control the regioselectivity and the enantiotopic face selection.
View Article and Find Full Text PDFOrganocatalytic Enantioselective Synthesis of [5.7]-Fused ε-Sultam ,-Heterocycles via (3 + 2)-Annulation of Seven-Membered Cyclic -Sulfonylimines with γ-Hydroxy-α,β-Unsaturated Ketones.
J Org Chem
December 2024
Henan Key Laboratory of Natural Medicine Innovation and Transformation, State Key Laboratory of Antiviral Drugs, Henan University, Kaifeng, Henan 475004, P. R. China.
A highly stereoselective protocol for the (3 + 2)-annulation of biphenyl-bridged seven-membered cyclic -sulfonylimines with γ-hydroxy-α,β-unsaturated ketones was developed. The reactions afforded a wide range of chiral [5.7]-fused ε-sultams bearing N-adjacent 1,3-stereocenters in excellent yields (93-98% yields) and high enantio/diastereoselectivities (up to >99% ee, >20:1 d.
View Article and Find Full Text PDFHTE-Enabled Development of an Ene-Reductase-Catalyzed Desymmetrization: Remote Control of All-Carbon Quaternary γ-Centers.
Org Lett
December 2024
Process Research & Development, MRL, Merck & Co., Inc., Rahway, New Jersey 07065, United States.
We report the remote stereocontrol of all-carbon quaternary γ-centers via an ene-reductase (ERED)-catalyzed desymmetrization of prochiral cyclohexadienones. By leveraging high-throughput experimentation (HTE) protocols, we were able to rapidly identify EREDs capable of desymmetrizing both spirocyclic cyclohexadienones and non-spirocyclic 2,6-disubstituted cyclohexadienone substrates in up to 85% yield with excellent levels of stereoselectivity (up to >99% ee and >20:1 dr) under mild reaction conditions.
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