Asymmetric Synthesis of Less Accessible α‐Tertiary Amines from Alkynyl Z‐Ketimines

2017/11/07 by Taichi Kano, Yusuke Aota, Keiji Maruoka · 3 citations
Chemistry · #Asymmetric Synthesis and Catalysis #Asymmetric Hydrogenation and Catalysis #Synthetic Organic Chemistry Methods

paper · doi:10.1002/anie.201710084

openalex publication_date 2017/11/07 · openalex created_date 2017/11/17 · openalex updated_date 2026/07/13

Abstract

A highly stereoselective synthesis of hitherto less accessible chiral α-tertiary amines with multiple structurally similar linear carbon chains was achieved through chiral auxiliary mediated addition of organolithium reagents to the geometrically well-controlled alkynyl Z-ketimines. This stereoselective nucleophilic addition offers a general approach to the asymmetric synthesis of nitrogen-containing chiral materials.

Cited by

• Construction of chiral α- tert -amine scaffolds via amine-catalyzed asymmetric Mannich reactions of alkyl-substituted ketimines
• Direct Catalytic Asymmetric Vinylogous Additions of α,β‐ and β,γ‐Butenolides to Polyfluorinated Alkynyl Ketimines
• Ketimine Mannich reaction [wikipedia]

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