A Convenient and Chemoselective One-Pot Oxidation/Wittig Reaction for the C2-Homologation of Carbohydrate-Derived Glycols
- 22 October 2005
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 70 (24) , 10099-10101
- https://doi.org/10.1021/jo051566e
Abstract
A simple and convenient one-pot protocol for the chemoselective C2-homologation of carbohydrate-derived glycols is described. The method comprises the chemoselective oxidation of the glycol to the corresponding hydroxyaldehyde and the subsequent Wittig alkenylation. In addition, the method does not need selective protective group manipulation, and it is safe, economical, fast (5 to 6 h), and bench-friendly. Its general utility is discussed.Keywords
This publication has 8 references indexed in Scilit:
- Synthesis and cation complexation properties of new macrolidesTetrahedron, 2005
- The cis-2-alkyl-3-oxy-tetrahydropyran unit as a building block for new ionophores with C2-symmetryTetrahedron Letters, 2004
- A sequential tetra-n-propylammonium perruthenate (TPAP)–Wittig oxidation olefination protocolTetrahedron Letters, 2003
- ONE-POT OXIDATION AND WITTIG OLEFINATION OF ALCOHOLS USING O-IODOXYBENZOIC ACID AND STABLE WITTIG YLIDE*Synthetic Communications, 2001
- Highly 1,2-trans Stereoselective Allylations of 1,2-O-Isopropylidene-Protected GlycofuranosidesAngewandte Chemie International Edition in English, 2000
- The Wittig olefination reaction and modifications involving phosphoryl-stabilized carbanions. Stereochemistry, mechanism, and selected synthetic aspectsChemical Reviews, 1989
- Application of the Swern oxidation to the manipulation of highly reactive carbonyl compoundsThe Journal of Organic Chemistry, 1985
- Complexes of bromine and iodine with bis-(diphenylglyoximato)nickel(II) and bis(diphenylglyoximato)palladium(II)Journal of the American Chemical Society, 1967