Atom-Economical and Stereoselective Difunctionalization of Electron-Withdrawing Alkynes with N-Trifluoromethylthiophthalimide

Juncheng Li, Zhiping Yang, Rui Guo, Ming Yu Jin, Jun Joelle Wang

Research output: Contribution to journalArticlepeer-review

Abstract

Difunctionalization: An N-methylmorpholine-catalyzed difunctionalization reaction of electron-withdrawing alkynes leading to α-SCF3-β-phthalimide unsaturated esters is described. N-Trifluoromethylthiophthalimide serves as both the nitrogen and SCF3 source. This difunctionalization reaction features high atom economy and excellent E/Z stereoselectivity.
An N-methylmorpholine-catalyzed aminotrifluoromethylthiolation of electron-withdrawing alkynes leads to α,β-unsaturated esters bearing a nitrogen and SCF3 groups. Here, N-trifluoromethylthiophthalimide serves as both the nitrogen and the SCF3 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 −SCF3-containing molecules (i. e. α-SCF3-β-amino acids).
Original languageEnglish
Pages (from-to)1784-1787
Number of pages4
JournalAsian Journal of Organic Chemistry
Volume7
Issue number9
DOIs
Publication statusPublished - Sep 2018

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