A Way to Highly Enantiomerically Enriched aza-Morita–Baylis–Hillman–Type Products

Authors

  • Naoto Utsumi Dr.,

    1. The Skaggs Institute for Chemical Biology and the Departments of Chemistry and Molecular Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA, Fax: (+1) 858-784-2583
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  • Haile Zhang Dr.,

    1. The Skaggs Institute for Chemical Biology and the Departments of Chemistry and Molecular Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA, Fax: (+1) 858-784-2583
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  • Fujie Tanaka Prof. Dr.,

    1. The Skaggs Institute for Chemical Biology and the Departments of Chemistry and Molecular Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA, Fax: (+1) 858-784-2583
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  • Carlos F. Barbas III Prof. Dr.

    1. The Skaggs Institute for Chemical Biology and the Departments of Chemistry and Molecular Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA, Fax: (+1) 858-784-2583
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  • This study was supported in part by The Skaggs Institute for Chemical Biology.

Abstract

original image

Schwierig zu synthetisierende β-Aminocarbonylverbindungen mit α-Alkylidengruppen sind enantioselektiv (bis 99 % ee) aus β-substituierten α,β-ungesättigten Aldehyden und α-Iminoestern in Gegenwart von (S)-Prolin und Imidazol unter milden Bedingungen zugänglich (siehe Schema, PMP=p-Methoxyphenyl). Als Teil des Reaktionsmechanismus wird eine Sequenz aus einer Mannich-Reaktion und einer Isomerisierung postuliert.

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