Woodward cw-dihydroxylation

Name Reactions, 4th ed., DOI 10.1007/978-3-642-01053-8 275, Springer-Verlag Berlin Heidelberg 2009 

Mergott, D. J. Woodward cis-dihydroxylation. In Name Reactions for Functional Group Transformations-, Li, J. J., Corey, E. J., Eds. John Wdey Sons Hoboken, NJ, 2007, pp 327-332. (Review). 

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One of the most useful modifications of the Woodward dihydroxylation was published by Cambie and Rutledge.12 This modification employs TIOAc in place of AgOAc and describes complementary procedures for the synthesis of cw-diols (Woodward reaction) and frans-diols (Provost reaction).13 Thus, treatment of cyclohexene 13 with TIOAc and I2 in HOAc at 80 °C, followed by the addition of water, affords acetate 14. Hydrolysis of 14 then gives cw-diol 15 in 70-75% yield. On the other hand, exposure of cyclohexene 13 to TIOAc, I2, and HOAc at reflux in the absence of water affords bis-acetate 16, which upon hydrolysis gives /raw-diol 17. 

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