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Forming All‐Carbon Quaternary Stereocenters by Organocatalytic Aminomethylation: Concise Access to β 2,2 ‐Amino Acids
Author(s) -
Wang Kai,
Yu Jianliang,
Shao Ying,
Tang Shengbiao,
Sun Jiangtao
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202009892
Subject(s) - stereocenter , enantioselective synthesis , organocatalysis , chemistry , amino acid , catalysis , enantiomer , phosphoric acid , stereochemistry , asymmetric carbon , carbon fibers , combinatorial chemistry , organic chemistry , optically active , biochemistry , materials science , composite number , composite material
Abstract The asymmetric synthesis of β 2,2 ‐amino acids remains a formidable challenge in organic synthesis. Here a novel organocatalytic enantioselective aminomethylation of ketenes with stable and readily available N,O‐acetals is reported, providing β 2,2 ‐amino esters bearing an all‐carbon quaternary stereogenic center in high enantiomeric ratios with a catalytic amount of chiral phosphoric acid. Typically, this transformation probably proceeds through an asymmetric counter‐anion‐directed catalysis. As a result, a concise, practical, and atom‐economic protocol toward rapidly access to β 2,2 ‐amino acids has been developed.