[1,2] Stevens sigmatropic rearrangement of pyrrolidinium ylides—simple synthesis of 3-aryl-2-cyano-1-methylpiperidines
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Add time:08/23/2019 Source:sciencedirect.com
Easily available N-cyanomethyl-N-methyl-2-arylpyrrolidinium salts treated with a base undergo ring expansion ([1,2]-Stevens rearrangement) with formation of new cis,trans-3-aryl-2-cyano-1-methylpiperidines. All reactions were performed under mild conditions and usually proceed in good yield. cis-Diastereoisomers of the products were isolated. The products and the starting intermediate quaternary salts are formed as mixture of diastereoisomers, their structures being unequivocally proved by NMR spectroscopy and X-ray analysis.
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