The Asymmetric Aza-silyl-Prins Reaction: Synthesis of Enantiopure Piperidines

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Abstract

The design and development of the first asymmetric aza-silyl-Prins reaction is reported, giving rise to valuable and diverse piperidines and pipecolic acid derivatives in both high yields and as single enantiomers. The creation of a novel chiral auxiliary-homoallylic amine for the aza-silyl-Prins reaction is essential to its success.

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Mittapalli, R. R., Guesné, S. J. J., Parker, R. J., Klooster, W. T., Coles, S. J., Skidmore, J., & Dobbs, A. P. (2019). The Asymmetric Aza-silyl-Prins Reaction: Synthesis of Enantiopure Piperidines. Organic Letters, 21(2), 350–355. https://doi.org/10.1021/acs.orglett.8b03283

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