Tuning diastereoselectivity is a great challenge in asymmetric catalysis for the inherent stereochemical bias of the substrates. Here, we report a diastereodivergent asymmetric Mannich reaction of cyclic N-sulfonyl ketimines with...
A highly
enantioselective three-component reaction of ynamides
with carboxylic acids and 2,2′-diester aziridines has been
realized by using a chiral N,N′-dioxide/Ho(OTf)3 complex as a Lewis acid catalyst. The process includes the
formation of an α-acyloxyenamide intermediate through the addition
of carboxylic acids to ynamides and the following enantioselective
nucleophilic addition to in-situ-generated azomethine
ylides induced by the chiral catalyst. A range of amino acyloxyenamides
are delivered in moderate to good yields with good ee values. In addition,
a possible catalytic cycle with a transition model is proposed to
elucidate the reaction mechanism.
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