Reduction of N-(phenylsulfonyl) pyrroles with sodium cyanoborohydride in trifluoroacetic acid

DM Ketcha, KP Carpenter, Q Zhou

文献索引：Ketcha, Daniel M.; Carpenter, Kenneth P.; Zhou, Qin Journal of Organic Chemistry, 1991 , vol. 56, # 3 p. 1318 - 1320

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被引用次数: 16

摘要

Due to the*-excessive character of the indole and pyrrole ring systems, these compounds are impervious to nucleophilic reducing species such as hydride reagents.'S2 However, partial reduction of these heterocycles can be accomplished but only under acidic conditions via a sequence involving initial protonation (at C-3 for indoles and predominantly at C-2 for pyrroles), followed by reduction of the resultant iminium intermediates. Whereas indoles ...