The para-siletanylbenzyl (PSB) ether: a peroxide-cleavable protecting group for alcohols and phenols |
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| Authors: | Hubert Lam |
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| Affiliation: | Department of Chemistry and Biochemistry, Florida State University, Tallahassee, FL 32306, USA |
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| Abstract: | A novel arylmethyl protecting group that is electronically similar to benzyl (Bn) but that can be cleaved under mild oxidizing conditions in the presence of para-methoxybenzyl (PMB) is described herein. para-Siletanylbenzyl (PSB) ethers are formed in one or two steps from the corresponding alcohols and cleaved in one or two steps with basic peroxide. Alcohols and phenols have been protected in good yields and deprotected cleanly under mild oxidative conditions. |
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| Keywords: | Benzyl Protecting group Siletane Oxidation Strained silacycle |
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