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The Ti(O- i Pr) 4 and EtMgBr-catalyzed regio and stereoselective carbocyclization of N -allyl-substituted 2-alkynylamines with Et 2 Zn, followed by deuterolysis or hydrolysis, affords the corresponding methylenepyrrolidine derivatives in high yields. It was found that Ti-Mg-catalyzed carbocyclization of N -allyl-substituted 2-alkynylamines with Et 2 Zn is equally selective in dichloromethane, hexane, toluene, and diethyl ether. The reaction was tolerant to the presence of aryl, alkyl, trimethylsilyl, methoxymethyl and aminomethyl substituents on the alkyne. A selective method was proposed for the preparation of bis-pyrrolidine derivatives using Ti-Mg-catalyzed carbocyclization of bis-allylpropargyl amines with Et 2 Zn.

rsc advances

Synthesis of heteroatom-containing pyrrolidine derivatives based on Ti(O-iPr)4 and EtMgBr-catalyzed carbocyclization of allylpropargyl amines with Et2Zn