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

Atom‐Economical and Stereoselective Difunctionalization of Electron‐Withdrawing Alkynes with... 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). http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Asian Journal of Organic Chemistry Wiley

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

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References (69)

Publisher
Wiley
Copyright
© 2018 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim
ISSN
2193-5807
eISSN
2193-5815
DOI
10.1002/ajoc.201800351
Publisher site
See Article on Publisher Site

Abstract

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).

Journal

Asian Journal of Organic ChemistryWiley

Published: Sep 1, 2018

Keywords: ; ; ; ;

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