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Combinatorial Chemistry & High Throughput Screening

Editor-in-Chief

ISSN (Print): 1386-2073
ISSN (Online): 1875-5402

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

Author(s): J. M. White, A. R. Tunoori, D. Dutta and G. I. Georg

Volume 3, Issue 2, 2000

Page: [103 - 106] Pages: 4

DOI: 10.2174/1386207003331706

Price: $65

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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

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