4-Fluoro-2,4-methanoproline

Anton N Tkachenko; Dmytro S Radchenko; Pavel K Mykhailiuk; Oleksandr O Grygorenko; Igor V Komarov

doi:10.1021/ol902381w

4-Fluoro-2,4-methanoproline

Org Lett. 2009 Dec 17;11(24):5674-6. doi: 10.1021/ol902381w.

Authors

Anton N Tkachenko¹, Dmytro S Radchenko, Pavel K Mykhailiuk, Oleksandr O Grygorenko, Igor V Komarov

Affiliation

¹ Department of Chemistry, Kyiv National Taras Shevchenko University, Vul. Volodymyrska 64, 01033 Kyiv, Ukraine.

PMID: 19904924
DOI: 10.1021/ol902381w

Abstract

The first fluorinated analogue of the naturally occurring 2,4-methanoproline, 4-fluoro-2,4-methanoproline, has been synthesized in five steps from commercially available methyl 2-fluoroacrylate through a photochemical cyclization as a key step in generating a 2-azabicyclo[2.1.1]hexane skeleton.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Azabicyclo Compounds / chemical synthesis*
Azabicyclo Compounds / chemistry
Catalysis
Cyclization
Hydrocarbons, Fluorinated / chemical synthesis*
Hydrocarbons, Fluorinated / chemistry
Molecular Structure
Proline / analogs & derivatives*
Proline / chemical synthesis
Proline / chemistry*

Substances

Azabicyclo Compounds
Hydrocarbons, Fluorinated
Proline