Control of N-Heterocyclic Carbene Catalyzed Reactions of Enals: Asymmetric Synthesis of Oxindole-γ-Amino Acid Derivatives
Chen, X.-Y., Xiong, J.-W., Liu, Q., Li, S., Sheng, H., von Essen, C., Rissanen, K., & Enders, D. (2018). Control of N-Heterocyclic Carbene Catalyzed Reactions of Enals: Asymmetric Synthesis of Oxindole-γ-Amino Acid Derivatives. Angewandte Chemie International Edition, 57(1), 300-304. https://doi.org/10.1002/anie.201708994
Published inAngewandte Chemie International Edition
Li, Sun |
© 2018 Wiley-VCH Verlag GmbH &Co.
A strategy to control the switch between a non‐cycloaddition reaction and a cycloaddition reaction of enals, using N‐heterocyclic carbene (NHC) catalyisis, has been developed. The new scalable protocol leads to γ‐amino‐acid esters bearing a tetrasubstituted stereocenter in good yields and high stereoselectivities by homo‐Mannich reactions of enals and isatin‐derived ketimines. By simply changing the N‐ketimine substituent to an ortho‐hydroxy phenyl group, the corresponding spirocyclic oxindolo‐γ‐lactams are obtained.
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