"Metalated nitriles: S<sub>N</sub>i′ cyclizations with a propargylic el" by Ping Lu, Venkata S. Pakkala et al.
 

Metalated nitriles: SNi′ cyclizations with a propargylic electrophile

Citation for published article

Coupled Hemodynamics and Oxygen Diffusion in Abdominal Aortic Aneurysm: A Computational Sensitivity Study

DOI

10.1016/j.tetlet.2015.01.013

Document Type

Journal Article

Publication Date

5-25-2015

Publication Title

Tetrahedron Letters

Keywords

5-exo-Dig, Hydrindane, Metalated nitriles, S i′ cyclization N

School

Bayer School of Natural and Environmental Sciences

Abstract

© 2015. Abstract A rare 5-exo-dig SNi′ cyclization with magnesiated and lithiated nitriles affords a cis-fused hydrindane bearing an exocyclic allene. The cyclization of the dilithiated nitrile pits a stereoelectronic preference for a trans-hydrindane against a cyclization through a less strained transition structure to the corresponding cis-hydrindane. Computational modeling suggests that the dilithiated nitrile cyclizes to a cis-hydrindane because the preferred transition structure positions the lithium cation in a cone of electron density that bridges the nitrile-bearing carbon, an alkoxide, and an electron-rich alkyne functionality.

Plum Print visual indicator of research metrics
PlumX Metrics
  • Citations
    • Citation Indexes: 3
  • Usage
    • Abstract Views: 5
  • Captures
    • Readers: 4
see details

Share

COinS