Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 68, Issue 20, Pages 7853-7861Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo034850j
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A general and regioselective synthesis of substituted pyrroles 2 by cycloisomerization of readily available (Z)-(2-en-4-ynyl)amines I is reported. Spontaneous cycloisomerization leading to 2 occurred in the course of preparation of enynamines bearing a terminal triple bond or a triple bond substituted with a phenyl or a CH2OTHP group. When the triple bond was substituted with an alkyl or alkenyl group, enynamines were stable and could be converted into the corresponding pyrroles by metal catalysis. CuCl2 was found to be an excellent catalyst for cycloisomerization of substrates substituted at C-3, while PdX2 in conjunction with KX (X = Cl, I) turned out to be a superior catalyst for the reaction of enynamines unsubstituted at C-3.
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