Work

Transition Metal‐Free Vinylcyclopropanation of Olefins via Carbolithiation Reactions: Synthesis of 3‐Azabicyclo[3.1.0]hexanes

Year: 2026

Type: article

Abstract: A formal vinylcyclopropanation of olefins from N ‐allyl N ‐(3‐alkoxymethyl‐2‐lithioallyl) amines acting as carbenoid equivalents is described. The reaction proceeds through a tandem 5‐ exo carbolithiation/3‐ exo S N ʹ affording 1‐vinylazabicyclo[3.1.0]hexanes. Different substituents can be located at any of the other positions of the azabicycle, leading in most cases to high diastereoselectivities. DFT studies have been performed to account for the observed stereoselectivities that could not be rationalized in all cases through the expected chair‐like transition states.

Source: Advanced Synthesis & Catalysis

DOI: 10.1002/adsc.70724

Authors: Nuria Cases, Marta Solas, M. Pilar Castroviejo, Samuel Suárez‐Pantiga, Miguel A. Rodríguez, Roberto Sanz

Institutions: Universidad de Burgos, Universidad de La Rioja

Language: English

Topic: Cyclopropane Reaction Mechanisms

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,650

Funders: Ministerio de Ciencia, Innovación y Universidades, Consejería de Educación, Junta de Castilla y León