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Synfacts 2008(9): 1002-1002  
DOI: 10.1055/s-2008-1078659
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Umpolung Reaction via Polymer-Supported Dithianes

Contributor(s): Yasuhiro Uozumi, Noboru Kobayashi
V. Bertini, F. Lucchesini*, M. Pocci, S. Alfei, B. Idini
Università di Genova, Italy
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Publication History

Publication Date:
22 August 2008 (online)

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Significance

Polymer-supported acyl anion equivalents of aldehydes (RCHO) were generated via dithiane formation with polymeric dithiol P1 and the subsequent treatment with BuLi. Resulting lithiated polymeric dithiane P2Li reacted with R¢CHO to give the corresponding alkylated dithiane P3. The cleavage of the 1,3-dithiane unit in P3 was performed with Hg(II) perchlorate hydrate or NBS to afford α-hydroxyketone 1 (up to 72% yield) along with diketone 2.