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. Author manuscript; available in PMC: 2012 May 15.
Published in final edited form as: J Am Chem Soc. 2010 Nov 15;132(48):17092–17095. doi: 10.1021/ja1086547

Table 3.

Tamao-Fleming oxidation of benzoxasilolesa

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a

Conditions: a. 7 or 8 (1 equiv), KHCO3 (2.0 equiv), 30% H2O2 (8.0 equiv), 1:1 THF/MeOH, rt; b. Ac2O (3.0 equiv), 2:1 CH2Cl2/Et3N, rt; c. TBSCl (2.5 equiv), imidazole (3.0 equiv), DMF, rt; d. BnBr (1.25 equiv), K2CO3 (1.5 equiv), TBAI (0.1 equiv), acetone, 65 °C; isolated yields (over 2 steps) for reactions conducted on 0.50 mmol scale following purification by silica gel chromatography.

b

Oxidation conducted at 40 °C.