Metal free regio – and stereoselective semireduction of CF<sub>3</sub>-substituted <i>N</i>-allenamides-Reference-Cited by-同舟云学术

Metal free regio – and stereoselective semireduction of CF₃-substituted N-allenamides

Published:2024 Issue:5 Volume:22 Page:940-944
ISSN:1477-0520
Container-title:Organic & Biomolecular Chemistry
language:en
Short-container-title:Org. Biomol. Chem.

Author:

Gommenginger Clément¹^ORCID,Hourtoule Maxime¹^ORCID,Menghini Marco¹^ORCID,Miesch Laurence¹^ORCID

Affiliation:

1. Equipe Synthèse Organique et Phytochimie, Institut de Chimie, CNRS-UdS, UMR 7177, 4 rue Blaise Pascal, CS 90032, 67081 Strasbourg, France

Abstract

A chemoselective metal-free 1,2-and 2,3-semireduction of CF3-substituted N-allenamides was developed. The enamide moiety could be reduced by Et3SiH/BF3·OEt2, while DBU promoted the stereoselective isomerization of the resulting allyl amides.

Funder

Centre National de la Recherche Scientifique

Université de Strasbourg

Publisher

Royal Society of Chemistry (RSC)

Subject

Organic Chemistry,Physical and Theoretical Chemistry,Biochemistry

Link

http://pubs.rsc.org/en/content/articlepdf/2024/OB/D3OB01859H

Reference35 articles.

1. Regiodivergent Synthesis of 1,3- and 1,4-Enynes through Kinetically Favored Hydropalladation and Ligand-Enforced Carbopalladation

2. Synthesis and Reactivity of N-Allenyl Cyanamides

3. Palladium-Catalyzed Domino Allenamide Carbopalladation/Direct C–H Allylation of Heteroarenes: Synthesis of Primprinine and Papaverine Analogues

4. Regio- and Stereoselective Copper-Catalyzed Allylation of 1,3-Dicarbonyl Compounds with Terminal Allenes

5. Gold(I)-Catalyzed Enantioselective Annulations between Allenes and Alkene-Tethered Oxime Ethers: A Straight Entry to Highly Substituted Piperidines and aza-Bridged Medium-Sized Carbocycles