The Asymmetric Synthesis of Amines via Nickel-Catalyzed Enantioconvergent Substitution Reactions.

ABSTRACT: Chiral dialkyl carbinamines are important in fields such as organic chemistry, pharmaceutical chemistry, and biochemistry, serving for example as bioactive molecules, chiral ligands, and chiral catalysts. Unfortunately, most catalytic asymmetric methods for synthesizing dialkyl carbinamines do not provide general access to amines wherein the two alkyl groups are of similar size (e.g., CH₂R versus CH₂R¹). Herein, we report two mild methods for the catalytic enantioconvergent synthesis of protected dialkyl carbinamines, both of which use a chiral nickel catalyst to couple an alkylzinc reagent (1.1-1.2 equiv) with a racemic partner, specifically, an α-phthalimido alkyl chloride or an N-hydroxyphthalimide (NHP) ester of a protected α-amino acid. The meth

SUBMITTER: Yang ZP 

PROVIDER: S-EPMC8336453 | biostudies-literature | 2021 Feb

REPOSITORIES: biostudies-literature