The application discloses a method for synthesizing an alpha-position chiral
nitrogen heteroaromatic ring under the
synergistic catalysis of a chiral
phosphoric acid and a Lewis acid, and the method comprises the following steps: taking a
nitrogen heteroaromatic ring olefin I as an electrophilic
reagent, taking an
aryl alkyl boronic acid II as a carbon
nucleophile, and under the
synergistic catalysis of a Lewis acid catalyst and a chiral
phosphoric acid catalyst, in the presence of an
organic solvent, an additive and a
proton source, performing a conjugate addition-asymmetric
protonation reaction to generate an alpha-position chiral
nitrogen heteroaromatic compound shown in formula V, and the reaction is shown as follows: The application provides a conjugate addition-asymmetric
protonation strategy for a nitrogen heteroaromatic ring olefin, which is synergistically catalyzed by a chiral
phosphoric acid and a Lewis acid (Fe(OTs)3) and involves an organic
boron reagent, a series of alpha-position chiral nitrogen heteroaromatic compounds are successfully synthesized by using the catalytic
system, the highest enantioselectivity reaches 98% ee, and good universality is shown for
aryl, heterocyclic and polysubstituted substrates, and the
bottleneck problem of low reactivity of 1,1-disubstituted substrates in a traditional method is effectively overcome.