Concepedia

Synthesis of Fluorinated <i>exo</i>‐Glycals through Modified Julia Olefination

Samuel Habib, Florent Larnaud, Emmanuel Pfund, Thierry Lequeux, Bernard Fenêt, Peter G. Goekjian, David Gueyrard

European Journal of Organic Chemistry · 2013 · 30 citations · 38 references

DOI

Concepts

Abstract

Abstract An efficient synthesis of fluorinated enol ethers derived from carbohydrates is reported. A modified Julia olefination reaction of functionalized lactones with fluorine‐substituted sulfones gives the corresponding monofluorinated tri‐ or tetrasubstituted exo ‐glycals.

References

38

The modified Julia olefination: alkene synthesis via the condensation of metallated heteroarylalkylsulfones with carbonyl compounds

Paul R. Blakemore · Journal of the Chemical Society Perkin Transactions 1 · 2002 · 639 citations

, , +2

A direct synthesis of olefins by reaction of carbonyl compounds with lithio derivatives of 2-[alkyl- or (2′-alkenyl)- or benzyl-sulfonyl]-benzothiazoles.

J.‐B. BAUDIN, Georges Hareau, S. A. JULIA et al. · Tetrahedron Letters · 1991 · 381 citations

, , +5

Synthetic Methods for Fluorinated Olefins

Hikaru Yanai, Takeo Taguchi · European Journal of Organic Chemistry · 2011 · 188 citations

, , +7

A facile transformation of sugar lactones to azasugars

Herman S. Overkleeft, Jim van Wiltenburg, Upendra K. Pandit · Tetrahedron · 1994 · 122 citations

, , +8

4',5'-Unsaturated-5'-fluoro adenosine nucleosides: potent mechanism-based inhibitors of S-adenosyl-L-homocysteine hydrolase

James R. McCarthy, Esa T. Jarvi, Donald P. Matthews et al. · Journal of the American Chemical Society · 1989 · 98 citations

, , +9