Lithium Chloride Catalyzed Asymmetric Domino Aza‐Michael Addition/[3 + 2] Cycloaddition Reactions for the Synthesis of Spiro‐ and Bicyclic α, β, γ‐Triamino Acid Derivatives. Issue 37 (17th August 2018)

• Record Type: Journal Article
• Authors: Just, David; Hernandez‐Guerra, Daniel; Kritsch, Susanne; Pohl, Radek; Císařová, Ivana; Jones, Peter G.; Mackman, Richard; Bahador, Gina; Jahn, Ullrich
• Other Names: Hostomský Zdeněk guestEditor.
• Is Part Of: European journal of organic chemistry. Issue 37(2018)
• Page Start: 5213
• Page End: 5221
• Publication Date: 2018-08-17
• Subjects: Tandem reactions -- Nitrogen heterocycles -- Non‐natural amino acids -- β‐Prolines -- Michael addition -- Diazo transfer -- 1, 3 Dipolar cycloaddition; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201800585
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : Angularly and peri‐fused tricyclic pyrrolidinopyrazolines are efficiently prepared by LiCl‐catalyzed domino aza‐Michael addition‐1, 3‐dipolar cycloaddition reactions. The absolute stereochemistry is controlled in the aza‐Michael addition step, nonaflyl azide serves as effective diazo transfer reagent to the formed enolate and the resulting diazo dipole engages in the 1, 3‐dipolar cycloaddition step. The resulting tricyclic pyrrolidinopyrazolines can be easily transformed to enantiomerically enriched nonproteinogenic spirocyclic α, β, γ‐triamino acids, angularly or peri‐fused tricyclic β‐prolines or pyrimidines. The activity of the tricyclic amino acid derivatives against the hepatitis C virus was determined. Abstract : Angularly and peri‐fused tricyclic pyrrolidinopyrazolines are efficiently prepared by LiCl catalyzed domino aza‐Michael addition‐1, 3‐dipolar cycloaddition. The resulting tricyclic pyrrolidinopyrazolines can be easily transformed to spirocyclic or condensed bicyclic α, β, γ‐triamino acid derivatives.