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Ben Jamaa A, Grellepois F. Diastereoselective Ritter-like Reaction on Cyclic Trifluoromethylated N,O-Acetals Derived from l-Tartaric Acid. J Org Chem. 2017;82(19):10360-10375doi: 10.1021/acs.joc.7b01814.
Ben Jamaa, A., & Grellepois, F. (2017). Diastereoselective Ritter-like Reaction on Cyclic Trifluoromethylated N,O-Acetals Derived from l-Tartaric Acid. The Journal of organic chemistry, 82(19), 10360-10375. https://doi.org/10.1021/acs.joc.7b01814
Ben Jamaa, Abdelkhalek, and Grellepois, Fabienne. "Diastereoselective Ritter-like Reaction on Cyclic Trifluoromethylated N,O-Acetals Derived from l-Tartaric Acid." The Journal of organic chemistry vol. 82,19 (2017): 10360-10375. doi: https://doi.org/10.1021/acs.joc.7b01814
Ben Jamaa A, Grellepois F. Diastereoselective Ritter-like Reaction on Cyclic Trifluoromethylated N,O-Acetals Derived from l-Tartaric Acid. J Org Chem. 2017 Oct 06;82(19):10360-10375. doi: 10.1021/acs.joc.7b01814. Epub 2017 Sep 08. PMID: 28885838.
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J Org Chem. 2017 Oct 06;82(19):10360-10375. doi: 10.1021/acs.joc.7b01814. Epub 2017 Sep 08.

Diastereoselective Ritter-like Reaction on Cyclic Trifluoromethylated N,O-Acetals Derived from l-Tartaric Acid.

The Journal of organic chemistry

Abdelkhalek Ben Jamaa, Fabienne Grellepois

Affiliations

  1. Université de Reims Champagne-Ardenne, Institut de Chimie Moléculaire de Reims , CNRS UMR 7312, UFR des Sciences Exactes et Naturelles, BP 1039, 51687 Reims Cedex 2, France.

PMID: 28885838 DOI: 10.1021/acs.joc.7b01814

Abstract

Despite the presence of the highly electron-withdrawing fluorinated substituent, cyclic α-trifluoromethylated N-acyliminium ions were successfully generated from fluorinated O-acetyl-N,O-acetal l-tartaric acid derivatives. The addition of nitriles on these intermediates occurred with high to excellent syn diastereoselectivity and led, in most cases, to oxazolines and amides as single diastereomers. The diastereoselectivity of the addition and the nature of the reaction product depend on the substituents on the hydroxyl groups of the tartaric acid scaffold. This methodology gave access to enantiopure, highly functionalized 5-(trifluoromethyl)pyrrolidin-2-one derivatives, bearing the fluorinated substituent on a tetrasubstituted carbon.

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