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Atom‐Economical and Stereoselective Difunctionalization of Electron‐Withdrawing Alkynes with N ‐Trifluoromethylthiophthalimide
Author(s) -
Li Juncheng,
Yang Zhiping,
Guo Rui,
Jin Ming Yu,
Wang Jun Joelle
Publication year - 2018
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201800351
Subject(s) - chemistry , stereoselectivity , nitrogen atom , yield (engineering) , polar effect , nitrogen , catalysis , atom (system on chip) , medicinal chemistry , molecule , combinatorial chemistry , organic chemistry , ring (chemistry) , materials science , computer science , metallurgy , embedded system
An N ‐methylmorpholine‐catalyzed aminotrifluoromethylthiolation of electron‐withdrawing alkynes leads to α,β‐unsaturated esters bearing a nitrogen and SCF 3 groups. Here, N ‐trifluoromethylthiophthalimide serves as both the nitrogen and the SCF 3 source. This difunctionalization reaction features mild reaction conditions, high atom economy, good yield (up to 93%) and excellent stereoselectivity ( Z / E up to 28 : 1). This study provides a versatile approach for the synthesis of −SCF 3 ‐containing molecules (i. e. α‐SCF 3 ‐β‐amino acids).