Catalytic Cyclopropanation of Alkenes Using Diazo Compounds Generated in Situ. A Novel Route to 2-Arylcyclopropylamines

2001/08/01 by Varinder K. Aggarwal, Javier de Vicente, Roger V. Bonnert · 3 citations
Chemistry · #Cyclopropane Reaction Mechanisms

paper · doi:10.1021/ol0164177

openalex publication_date 2001/08/01 · openalex created_date 2025/10/10 · openalex updated_date 2026/08/01

Abstract

[reaction: see text]. A user-friendly, one-pot process for catalytic cyclopropanation of alkenes from tosylhydrazones is described. The cyclopropanation of N-vinylphthalimide provides a new route to 2-arylcyclopropylamines, and this is exemplified in the efficient synthesis of the HIV-1 reverse transcriptase inhibitor 6.

Cited by

• A New Protocol for the In Situ Generation of Aromatic, Heteroaromatic, and Unsaturated Diazo Compounds and Its Application in Catalytic and Asymmetric Epoxidation of Carbonyl Compounds. Extensive Studies To Map Out Scope and Limitations, and Rationalization of Diastereo- and Enantioselectivities
• The Use of Tosylhydrazone Salts as a Safe Alternative for Handling Diazo Compounds and Their Applications in Organic Synthesis
• Tosylhydrazone [wikipedia]