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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 international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202009892
Subject(s) - stereocenter , enantioselective synthesis , organocatalysis , chemistry , catalysis , phosphoric acid , amino acid , enantiomer , asymmetric carbon , carbon fibers , quaternary carbon , carbon atom , stereochemistry , combinatorial chemistry , organic chemistry , optically active , ring (chemistry) , mathematics , biochemistry , composite number , algorithm
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.