Direct Catalytic Asymmetric Mannich‐type Reaction of α,β‐Unsaturated γ‐Butyrolactam with Ketimines

2016/02/02 by Shaoquan Lin, Naoya Kumagai, Masakatsu Shibasaki · 2 citations
Chemistry · #Asymmetric Synthesis and Catalysis #Synthesis and Catalytic Reactions #Synthetic Organic Chemistry Methods

paper · doi:10.1002/chem.201600034

openalex publication_date 2016/02/02 · openalex created_date 2025/10/10 · openalex updated_date 2026/06/24

Abstract

We report a direct catalytic asymmetric Mannich-type addition of α,β-unsaturated γ-butyrolactam to α-ethoxycarbonyl ketimines promoted by a soft Lewis acid/Brønsted base cooperative catalyst. A thiophosphinoyl group on the nitrogen of ketimines was crucial for both electrophilic activation and α-addition of γ-butyrolactams. The obtained aza-Morita-Baylis-Hillman-type products bear an α-amino acid architecture with a tetra-substituted stereogenic center.

Citations

• aza-Baylis−Hillman Reaction
• Recent Contributions from the Baylis−Hillman Reaction to Organic Chemistry
• The Vinylogous Aldol Reaction: A Valuable, Yet Understated Carbon−Carbon Bond-Forming Maneuver

Cited by

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