A new ring synthesis for 3-and polysubstituted furans; directing effects of a 3-(arenesulfonyl) group in metalation and Friedel-Crafts processes
SW McCombie, BB Shankar, AK Ganguly
Index: McCombie, S. W.; Shankar, B. B.; Ganguly, A. K. Tetrahedron Letters, 1987 , vol. 28, # 36 p. 4123 - 4126
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Citation Number: 23
Abstract
Abstract Primary and secondary α-bromoketones react with the potassium salt (3) to afford 2- [E-2-(p-toluenesulfonyl)-ethenyloxy]-ketones. On treatment with LDA followed by p-TsOH, good yields of the corresponding 3-or 2, 3-substituted-4-tosylfuran are obtained, from which the 4-substituent may be reductively removed. 3-Aryl or alkyl-4-tosylfurans undergo regiospecific metalation at C-5 and Friedel-Crafts acylation at C-2. These processes ...
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