Catalytic Asymmetric Addition Reactions of Formaldehyde N,N‑Dialkylhydrazone to Synthesize
Chiral Nitrile Derivatives
Posted on 2020-06-11 - 17:07
A number
of nitrile-containing chiral molecules were synthesized via asymmetric
nucleophilic addition of formaldehyde N,N-dialkylhydrazone as the nitrile equivalent. Chiral N,N′-dioxide/metal salt complexes enabled the asymmetric addition
reactions to both isatin-derived imines and α,β-unsaturated
ketones, generating amino nitriles and 4-oxobutanenitrile derivatives
in good yields with high enantioselectivities. This protocol was highlighted
by avoiding the use of toxic nitrile reagents, wide substrate scope,
and versatile transformations of chiral hydrazone adducts into other
valuable molecules.
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