The use of polymer-bound triphenylphosphine in the stereochemical inversion of secondary alcohols.
Polymer-bound triphenylphosphine can replace triphenylphosphine in the Mitsunobu reaction to generate stereochemically inverted secondary alcohols. This method is comparable with the standard Mitsunobu reaction in terms of inversion of stereochemistry, yield, and reaction time, even for sterically very hindered secondary alcohols. The special merit of this reaction is that the excess polymer-bound triphenylphosphine and its by-products are easily removed by filtration from the reaction products.
White
J M
JM
Department of Medicinal Chemistry and The Drug Discovery Program, Higuchi Biosciences Center, University of Kansas, Lawrence, KS 66045, USA.
Tunoori
A R
AR
Dutta
D
D
Georg
G I
GI
D000438:Alcohols / Q000737:chemistry*; D015394:Molecular Structure; D009943:Organophosphorus Compounds / Q000737:chemistry*; D011108:Polymers / Q000737:chemistry*; D013237:Stereoisomerism
D000438:Alcohols; D009943:Organophosphorus Compounds; D011108:Polymers; C061896:triphenylphosphine