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 | Zendy

Kuroda Yusuke | Zendy; Harada Shingo | Zendy; Oonishi Akinori | Zendy; Kiyama Hiroki | Zendy; Yamaoka Yousuke | Zendy; Yamada Kenichi | Zendy; Takasu Kiyosei | Zendy

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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 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.

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