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Synfacts 2011(9): 1031-1031  
DOI: 10.1055/s-0030-1260897
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

The Mitsunobu Reaction with MPEG-Supported Ph3P and DEAD

Contributor(s): Yasuhiro Uozumi, Aya Tazawa
M. Figlus, N. Wellaway, W. J. Cooper, S. L. Sollis, R. C. Hartley*
University of Glasgow and GSK Medicines Centre, Stevenage, UK
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Publication History

Publication Date:
19 August 2011 (online)

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Significance

Triphenylphosphine (TPP) and diethyl azodicarboxylate (DEAD) supported on a low-molecular-weight poly-(ethyleneglycol)-ω-monomethylether (MTPP-G2, MDEAD) were prepared from MPEG-OH (eqs. 1 and 2). The ­Mitsunobu reaction of alcohols with phenols, ­carboxylic acids and sulfonamide was performed with the polymeric reagents, MTPP-G2 and MDEAD. The resulting mixture was passed through silica gel to afford the corresponding products in up to 99% yield with up to 95% purity without any further purification (20 examples, eq. 3).