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Organocatalytic Enantioselective Synthesis of Chiral Diarylmethylamines from Racemic Alcohols
Author(s) -
Chen Min,
Han Yaodong,
Ma Dengke,
Wang Yong,
Lai Zengwei,
Sun Jianwei
Publication year - 2018
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201800135
Subject(s) - chemistry , enantioselective synthesis , kinetic resolution , substrate (aquarium) , derivatization , scope (computer science) , formal synthesis , organocatalysis , combinatorial chemistry , stereochemistry , organic chemistry , catalysis , oceanography , high performance liquid chromatography , geology , computer science , programming language
An organocatalytic approach for direct conversion of racemic diarylmethanols to valuable chiral diarylmethylamines is described. Different from the previously reported elegant “borrowing hydrogen” approach, the present process employs a distinct complementary formal S N 1 strategy. This approach enjoys excellent enantioselectivity, mild conditions, broad scope, and easy product derivatization. Mechanistically, control experiments also provided important insights into some notable features, such as substrate kinetic resolution and reversibility as well as the critical role of the ortho ‐ hydroxy group in the substrate.