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  • Highly enantioselective addition of enals to isatin-derived ketimines catalyzed by N-heterocyclic carbenes: synthesis of spirocyclic γ-lactams.

Highly enantioselective addition of enals to isatin-derived ketimines catalyzed by N-heterocyclic carbenes: synthesis of spirocyclic γ-lactams.

Organic letters (2012-10-16)
Hui Lv, Bhoopendra Tiwari, Junming Mo, Chong Xing, Yonggui Robin Chi
RESUMEN

An N-heterocyclic carbene (NHC)-catalyzed annulation reaction of isatin N-Boc ketimines and enals is developed for the synthesis of spirocyclic oxindole-γ-lactams bearing one quaternary chiral center in good yields and excellent stereoselectivities (up to >20:1 dr and 99% ee).

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Sigma-Aldrich
Isatin, 97%