Bifunctional NHC-Catalyzed Asymmetric Intramolecular Conjugate Addition via Noncovalent Interaction
Ujjwal Maji1, Arpita Baidya1, Supriyo Das1
1School of Chemical Sciences, Indian Association for the Cultivation of Science, 2A & 2B Raja S. C. Mullick Road, Jadavpur, Kolkata 700032, India.
Abstract:
Herein, we report a novel squaramide containing chiral bifunctional N-heterocyclic carbene (NHC) and its utilization in developing asymmetric intramolecular conjugate addition involving noncovalent interaction. Via concomitant activation of both electrophilic and nucleophilic centers of substrates, the reaction proceeds through a well-organized transition state, thereby affording products with up to 94% ee and a broad scope. The process is found to be scalable. The initial mechanistic study supports the bifunctional nature of the newly designed NHC.
More Related Videos
07:50Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
07:07Synthetic Methodology for Asymmetric Ferrocene Derived Bio-conjugate Systems via Solid Phase Resin-based Methodology
Published on: March 12, 2015
Related Concept Videos
Conjugate Addition to α,β-Unsaturated Carbonyl Compounds
Conjugate Addition (1,4-Addition) vs Direct Addition (1,2-Addition)
Conjugate addition results in a thermodynamically stable product. The reaction retains the stronger C=O bond at the expense of the weaker C=C π bond. The process is slow as the β carbon is less electrophilic than the carbonyl carbon.
Direct addition products are...
Conjugate Addition of Enolates: Michael Addition
Cycloaddition Reactions: MO Requirements for Thermal Activation
Electrophilic 1,2- and 1,4-Addition of HX to 1,3-Butadiene
Nucleophilic Aromatic Substitution: Elimination–Addition
