Cathodic hydroxylation of organoboron compounds was successfully performed under an oxygen atmosphere, producing the corresponding phenol derivatives with high selectivity and efficiency.

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Allyl mesityl sulfide reacted with ethyl glyoxylate in the presence of tin(IV) chloride to give a tetrahydrofuran derivative. The presence of a bulky substituent on the sulfur atom was crucial to the present reaction. The reaction of allyl mesityl selenide also gave a cycloaddition product, whereas allylation occurred when allyl mesityl telluride was used.

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Furan derivatives R 0060Lewis Acid Mediated Reactions of Allyl Chalcogenides with Ethyl Glyoxylate. -Allyl sulfides (I) react with glyoxylate (II) in the presence of a Lewis acid to give tetrahydrofuran derivatives (III). The presence of a bulky substituent on the sulfur is found to be crucial for the reaction. The analogous reaction of selenide (V) also affords a [3 + 2] cycloaddition product (VI)/(VII) as mixture of diastereomers. In contrast, allylation occurs when allyl mesityl telluride is used. -(HIRABAYASHI, K.; SATO, H.; KURIYAMA, Y.; MATSUO, J.-I.; SATO, S.; SHIMIZU*, T.; KAMIGATA, N.; Chem. Lett. 36 (2007) 7, 826-828; Dep. Chem., Grad. Sch. Sci., Tokyo Metrop. Univ., Hachioji, Tokyo 192-03, Japan; Eng.) -M. Paetzel 50-122