Understanding the Diastereopreference of Intermediates in Aminocatalysis: Application to the Chiral Resolution of Lactols
journal contribution
posted on 2021-02-11, 08:03 authored by Carla Alamillo-Ferrer, Christian D.-T. Nielsen, Andrea Salzano, Xavier Companyó, Riccardo Di Sanza, Alan C. Spivey, Henry S. Rzepa, Jordi BurésDownstream 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.
