Towards an Asymmetric β-Selective Addition of Azlactones to Allenoates

Submitting author affiliation:
Johannes Kepler University Linz, Linz, Austria

Beilstein Arch. 2024, 202428.

Published 06 May 2024

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This preprint has not been peer-reviewed. When a peer-reviewed version is available, this information will be updated.


We herein report the asymmetric organocatalytic addition of azlactones to allenoates. Upon using chiral quaternary ammonium salt catalysts, i.e. Maruoka’s binaphthyl-based spirocyclic ammonium salts, the addition of various azlactones to allenoates proceeds in a β-selective manner with moderate levels of enantioselectivities (up to 83:17 e.r.). Furthermore, the obtained products can be successfully engaged in nucleophilic ring opening reactions, thus giving highly functionalized α-amino acid derivatives.

Keywords: organocatalysis; quaternary ammonium salt catalysis; azlactones; allenoates; amino acids

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When a peer-reviewed version of this preprint is available, this information will be updated in the information box above. If no peer-reviewed version is available, please cite this preprint using the following information:

Nasiri, B.; Pasdar, G.; Zebrowski, P.; Röser, K.; Naderer, D.; Waser, M. Beilstein Arch. 2024, 202428. doi:10.3762/bxiv.2024.28.v1

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