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A Novel Chemoselective Cleavage of (tert‐Butyl)(dimethyl)silyl (TBS) Ethers Catalyzed by Ce(SO4)2⋅4 H2O |
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| Authors: | Davir González‐Calderón Carlos A González‐González Aydeé Fuentes‐Benítez Erick Cuevas‐Yáñez David Corona‐Becerril Carlos González‐Romero |
| Institution: | 1. Departamento de Química Orgánica, Facultad de Química, Universidad Autónoma del Estado de México, Paseo Colón/Paseo Tollocan s/n, Toluca, Estado de México, 50120, Mexico, (phone: +52‐722‐2175109 ext 113;2. fax: +52‐722‐2173890);3. Centro Conjunto de Investigación en Química Sustentable UAEM‐UNAM, Toluca‐Atlacomulco Km. 14.5, San Cayetano, Toluca, Estado de México, 50200, Mexico |
| Abstract: | (tert‐Butyl)(dimethyl)silyl (tBuMe2Si; TBS) phenyl/alkyl ethers were efficiently cleaved to the corresponding parent hydroxy compounds in good yields using catalytic amounts of Ce(SO4)2?4 H2O by microwave‐assisted or conventional heating in MeOH. Intramolecular and competitive experiments demonstrated the chemoselective deprotection of TBS ethers in the presence of triisopropylsilyl (iPr3Si; TIPS) and (tert‐butyl)(diphenyl)silyl (tBuPh2Si; TBDPS) ethers. |
| Keywords: | Alcohols Catalysis (tert‐Butyl)(dimethyl)silyl (TBS) ethers Cesium(IV) sulfate catalyst |