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

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

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 mole...

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Veröffentlicht in:Journal of organic chemistry 2021-03, Vol.86 (5), p.4326-4335
Hauptverfasser: Alamillo-Ferrer, Carla, Nielsen, Christian D.-T, Salzano, Andrea, Companyó, Xavier, Di Sanza, Riccardo, Spivey, Alan C, Rzepa, Henry S, Burés, Jordi
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container_end_page 4335
container_issue 5
container_start_page 4326
container_title Journal of organic chemistry
container_volume 86
creator Alamillo-Ferrer, Carla
Nielsen, Christian D.-T
Salzano, Andrea
Companyó, Xavier
Di Sanza, Riccardo
Spivey, Alan C
Rzepa, Henry S
Burés, Jordi
description 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.
doi_str_mv 10.1021/acs.joc.0c02998
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title Understanding the Diastereopreference of Intermediates in Aminocatalysis: Application to the Chiral Resolution of Lactols
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