BINOL Phosphoric Acid‐Catalyzed Asymmetric Mannich Reaction of Cyclic N‐Acyl Ketimines with Cyclic Enones

2019/06/26 by K. Nagarjuna Reddy, M. V. Rao, B. Sridhar +1 · 2 citations
Chemistry · #Asymmetric Synthesis and Catalysis #Asymmetric Hydrogenation and Catalysis #Synthetic Organic Chemistry Methods

paper · doi:10.1002/asia.201900556

openalex publication_date 2019/06/26 · openalex created_date 2019/07/12 · openalex updated_date 2026/07/27

Abstract

A highly enantio- and diastereoselective Mannich reaction of cyclic N-acyl ketimines generated in situ from 3-hydroxyisoindolin-1-ones with cyclic enones has been accomplished using a chiral phosphoric acid catalyst to afford the chiral isoindalinone derivatives in high yields with excellent enantioselectivities (upto 97 % ee). This is the first report on the synthesis of chiral isoindolin-1-ones bearing adjacent quaternary and tertiary stereogenic centers.

Citations

• Chiral Phosphoric Acids as Versatile Catalysts for Enantioselective Transformations

Cited by

• Construction of chiral α- tert -amine scaffolds via amine-catalyzed asymmetric Mannich reactions of alkyl-substituted ketimines
• Ketimine Mannich reaction [wikipedia]

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