Synfacts 2008(6): 0660-0660  
DOI: 10.1055/s-2008-1072632
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Dithiane Hydrolysis by a Polymer-Supported Iodate

Contributor(s): Yasuhiro Uozumi, Yoichi M. A. Yamada
S. Luiken, A. Kirschning
Leibniz Universität Hannover, Germany
Further Information

Publication History

Publication Date:
21 May 2008 (online)

Significance

The first solid-phase-assisted protocol for the hydrolysis of dithioacetals with three kinds of functionalized ion-exchange resins was described. Thus, the reaction of 1 with resin-supported 2 (4-10 mol equiv) in aqueous MeCN at room temperature for 0.5-1 hour followed by scavenging CF3CO2H with resin-supported 3 4-10 mol equiv) and removing dithiolane 8 with resin-supported 4 (4-10 mol equiv) afforded 5a-d in 83-94% yield. Additional purification was not necessary for the isolation of 5.