Bifunctional Organocatalysts for Enantioselective aza-Morita−Baylis−Hillman Reaction

2005/03/01 by Katsuya Matsui, Shinobu Takizawa, Hiroaki Sasai · 6 citations
Chemistry · Biochemistry, Genetics and Molecular Biology · #Asymmetric Synthesis and Catalysis #Chemical Synthesis and Analysis #Synthesis and Catalytic Reactions

paper · doi:10.1021/ja0500254

openalex publication_date 2005/03/01 · openalex created_date 2025/10/10 · openalex updated_date 2026/06/26

Abstract

The efficient and novel bifunctional organocatalyst for the enantioselective aza-Morita-Baylis-Hillman (aza-MBH) reaction has been established with (S)-3-(N-isopropyl-N-3-pyridinylaminomethyl)BINOL for the first time. The reaction proved to be deeply influenced by the position of the Lewis base attached to BINOL. The acid-base-mediated functionalities for the activation of the substrate and the fixing of conformation of the organocatalyst are harmoniously performed to promote the reaction with high enantiocontrol.

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• Bifunctional Activation and Racemization in the Catalytic Asymmetric Aza-Baylis−Hillman Reaction
• The Enantioselective Morita–Baylis–Hillman Reaction and Its Aza Counterpart
• Recent Contributions from the Baylis−Hillman Reaction to Organic Chemistry
• aza-Baylis−Hillman Reaction
• Lewis Base Catalysis in Organic Synthesis
• Aza-Baylis–Hillman reaction [wikipedia]