Premium
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 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.201607208
Subject(s) - kinetic resolution , catalysis , kinetic energy , group (periodic table) , carbon fibers , leaving group , chemistry , asymmetric carbon , resolution (logic) , stereochemistry , organic chemistry , enantioselective synthesis , materials science , physics , optically active , quantum mechanics , artificial intelligence , 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.