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Synfacts 2007(7): 0686-0686
DOI: 10.1055/s-2007-968676
DOI: 10.1055/s-2007-968676
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York
Gold-Catalyzed Synthesis of Pyrrolidones by an 5- and 6-exo-trig Cycloaddition Reaction
C.-Y. Zhou, C.-M. Che*
The University of Hong Kong, P. R. of China
Further Information
Publication History
Publication Date:
22 June 2007 (online)
Significance
A highly efficient Au-catalyzed synthesis of pyrrolidones and piperidines by intramolecular 5- or 6-exo-trig cyclization of β -keto amides to unactivated alkenes is reported. The substrates with internal alkenes give lower yields (61-67%) compared to those with terminal alkenes (90-99%). Interestingly, only one diastereomer is formed from both cis and trans alkenes. No 5- or 6-endo-trig products are observed although 6-endo-trig cyclization is favored according to Baldwin’s rules. The given mechanism is supported by deuterium labeling experiments.