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Expeditious Construction of Spiro‐Pyrrolidines by an Autocatalytic One‐Pot, Five‐Component, 1,3‐Dipolar Cycloaddition of in situ Generated Azomethine Ylides and Olefinic Dipolarophiles
Author(s) -
Li Ming,
Gong FuMeng,
Wen LiRong,
Li ZhaoRui
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201100297
Subject(s) - chemistry , azomethine ylide , malononitrile , cycloaddition , 1,3 dipolar cycloaddition , sarcosine , pyrrolidine , autocatalysis , ninhydrin , organic chemistry , cyanoacetic acid , isatin , combinatorial chemistry , catalysis , glycine , biochemistry , amino acid
Abstract Two series of previously unknown spiro‐pyrrolidine derivatives were prepared by a five‐component reaction that employed ninhydrin, 1,2‐phenylenediamine, sarcosine, aldehydes, and malononitrile or cyanoacetic ester in a solvothermal synthesis. This is the first report of an autocatalytic five‐component reaction involving a classical Huisgen reaction, in which the dipole – an azomethine ylide – and the dipolarophile were simultaneously generated in situ. The 1,3‐dipolar cycloaddition reaction was found to proceed in a highly regio‐ and diastereoselective manner. The methodology for the preparation of the spiro‐pyrrolidines could be an ideal tool for green chemistry and the synthesis of alkaloids.