(3 + 2) Cycloaddition Reaction of the Endocyclic N‑Silyl Enamine and N,N′-Cyclic Azomethine Imine

We describe the (3 + 2) cycloaddition reaction of endocyclic N-silyl enamines and N,N′-cyclic azomethine imines. This process utilized the versatile endocyclic N-silyl enamine intermediates from the dearomative hydrosilylation of N-heteroarenes. The resulting tetracyclic pyrazolidinone structure was...

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Bibliographic Details
Published in:Organic letters 2022-03, Vol.24 (10), p.1974-1978
Main Authors: Cao, Vinh Do, Kim, Huiae, Kwak, Jaesung, Joung, Seewon
Format: Article
Language:English
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Summary:We describe the (3 + 2) cycloaddition reaction of endocyclic N-silyl enamines and N,N′-cyclic azomethine imines. This process utilized the versatile endocyclic N-silyl enamine intermediates from the dearomative hydrosilylation of N-heteroarenes. The resulting tetracyclic pyrazolidinone structure was synthesized by a straightforward and atom-economical process. We also discussed the plausible origins of the different reactivity and endo/exo selectivity in terms of the structures of each proposed transition state. The successful gram-scale synthesis demonstrated the synthetic utility.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c00366