The cyclization of terminal alkynes with homopropargylic amines in the presence of a rhodium complex as catalyst leads to the formation of (E)-3-alkylidene-1-pyrrolines. The reaction tolerates a wide range of functional groups on the terminal alkynes. The formation of a vinylidene-rhodium complex, followed by the intermolecular nucleophilic attack of a homopropargylic amine nitrogen on the a-carbon atom of the vinylidene-rhodium complex, is proposed as a key step in the catalytic reaction.
Synthesis of (E)-3-Alkylidene-1-pyrrolines by the Rhodium-Catalyzed Cyclization of Terminal Alkynes with Homopropargylic Amines. -The title reaction tolerates a wide range of functional groups at the terminal alkyne but is sensitive towards steric hindrance. The reaction is proposed to proceed via a vinylidene-Rh complex which is attacked at the α-carbon by the homopropargylic amine nitrogen. -(FUKUMOTO*, Y.; KAWAHARA, T.; KANAZAWA, Y.; CHATANI, N.; Adv.
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