The Use of Polymer-Bound Triphenylphosphine in the Stereochemical Inversion of Secondary Alcohols

Authors: White J.M.; Tunoori A.R.; Dutta D.; Georg G.I.

Source: Combinatorial Chemistry & High Throughput Screening, Volume 3, Number 2, April 2000 , pp. 103-106(4)

Publisher: Bentham Science Publishers

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Abstract:

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.

Keywords: Polymer bound triphenylphosphine; Mitsunobu reaction; Diethyl azodicarboxylate; Lithium hydroxide; Tetrahydrofuran

Language: English

Document Type: Regular paper

DOI: 10.2174/1386207003331706

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