Understanding the Diastereopreference of Intermediates in Aminocatalysis: Application to the Chiral Resolution of Lactols

Carla Alamillo-ferrer, Christian D.-t. Nielsen, Andrea Salzano, Xavier Companyó, Riccardo Di Sanza, Alan C. Spivey, Henry S. Rzepa, Jordi Burés

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Abstract

Downstream intermediates are crucial for the reactivity and selectivity of aminocatalytic reactions. We present an analysis of the stereopreference in aminocatalytic downstream intermediates, which reveals an inconspicuous mechanism of chiral recognition between the catalyst and the rest of the molecule. We delineate a stereoelectronic model to rationalize the mode of chiral transmission. We also exploit it for the resolution of chiral lactols relevant in organic synthesis as well as in the flavor and fragrance industry.
Original languageEnglish
JournalThe Journal of organic chemistry
Early online date10 Feb 2021
DOIs
Publication statusPublished - 10 Feb 2021

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  • JB EPSRC NIA Nov18

    Bures, J.

    1/10/1830/09/20

    Project: Research

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