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Use of a Catalytic Chiral Leaving Group for Asymmetric Substitutions at sp 3 ‐Hybridized Carbon Atoms: Kinetic Resolution of β‐Amino Alcohols by p ‐Methoxybenzylation
Author(s) -
Kuroda Yusuke,
Harada Shingo,
Oonishi Akinori,
Kiyama Hiroki,
Yamaoka Yousuke,
Yamada Kenichi,
Takasu Kiyosei
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201607208
Subject(s) - kinetic resolution , phosphoric acid , steric effects , chemistry , catalysis , asymmetric carbon , carbon fibers , chirality (physics) , leaving group , amino acid , resolution (logic) , chiral resolution , combinatorial chemistry , enantioselective synthesis , stereochemistry , organic chemistry , optically active , chiral symmetry , materials science , enantiomer , biochemistry , nambu–jona lasinio model , physics , quantum mechanics , artificial intelligence , quark , composite number , computer science , composite material
Abstract A catalytic strategy was developed for asymmetric substitution reactions at sp 3 ‐hybridized carbon atoms by using a chiral alkylating agent generated in situ from trichloroacetimidate and a chiral phosphoric acid. The resulting chiral p ‐methoxybenzyl phosphate selectively reacts with β‐amino alcohols rather than those without a β‐NH functionality. The use of an electronically and sterically tuned chiral phosphoric acid enables the kinetic resolution of amino alcohols through p ‐methoxybenzylation with good enantioselectivity.
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