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Sequential Visible-Light Photoactivation and Palladium Catalysis Enabling Enantioselective [4+2] Cycloadditions.

Catalytic asymmetric cycloadditions of reactive ketene intermediates provide new opportunities for the production of chiral heterocyclic molecules. Though known for over 100 years, ketenes still remain underexplored in the field of transition-metal (TM)-catalyzed asymmetric cycloadditions because (1... Full description

Journal Title: Journal of the American Chemical Society October 18, 2017, Vol.139(41), pp.14707-14713
Main Author: Li, Miao-Miao
Other Authors: Wei, Yi , Liu, Jie , Chen, Hong-Wei , Lu, Liang-Qiu , Xiao, Wen-Jing
Format: Electronic Article Electronic Article
Language: English
ID: E-ISSN: 1520-5126 ; DOI: 1520-5126 ; DOI: 10.1021/jacs.7b08310
Link: http://search.proquest.com/docview/1944436741/?pq-origsite=primo
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title: Sequential Visible-Light Photoactivation and Palladium Catalysis Enabling Enantioselective [4+2] Cycloadditions.
format: Article
creator:
  • Li, Miao-Miao
  • Wei, Yi
  • Liu, Jie
  • Chen, Hong-Wei
  • Lu, Liang-Qiu
  • Xiao, Wen-Jing
ispartof: Journal of the American Chemical Society, October 18, 2017, Vol.139(41), pp.14707-14713
description: Catalytic asymmetric cycloadditions of reactive ketene intermediates provide new opportunities for the production of chiral heterocyclic molecules. Though known for over 100 years, ketenes still remain underexplored in the field of transition-metal (TM)-catalyzed asymmetric cycloadditions because (1) ketenes, as highly electron-deficient species, are possibly unstable to low-valence TMs (i.e., decarbonylation or aggregation) and (2) the conventional thermal synthesis of ketenes from acyl chlorides and amines may be incompatible with TM catalysis (i.e., reactive acyl chloride and amine hydrochloride byproducts). Herein, we detail the unprecedented asymmetric [4+2] cycloaddition of vinyl benzoxazinanones with a variety of ketene intermediates via sequential visible-light photoactivation and palladium catalysis. It is well demonstrated that the traceless and transient generation of ketenes from α-diazoketones through visible-light-induced Wolff rearrangement is important for the success of present cycloaddition. Furthermore, chiral palladium catalysts with a new, chiral hybrid P, S ligand enable asymmetric cycloaddition with high reaction selectivity and enantiocontrol.
language: eng
source:
identifier: E-ISSN: 1520-5126 ; DOI: 1520-5126 ; DOI: 10.1021/jacs.7b08310
fulltext: no_fulltext
issn:
  • 15205126
  • 1520-5126
url: Link


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titleSequential Visible-Light Photoactivation and Palladium Catalysis Enabling Enantioselective [4+2] Cycloadditions.
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descriptionCatalytic asymmetric cycloadditions of reactive ketene intermediates provide new opportunities for the production of chiral heterocyclic molecules. Though known for over 100 years, ketenes still remain underexplored in the field of transition-metal (TM)-catalyzed asymmetric cycloadditions because (1) ketenes, as highly electron-deficient species, are possibly unstable to low-valence TMs (i.e., decarbonylation or aggregation) and (2) the conventional thermal synthesis of ketenes from acyl chlorides and amines may be incompatible with TM catalysis (i.e., reactive acyl chloride and amine hydrochloride byproducts). Herein, we detail the unprecedented asymmetric [4+2] cycloaddition of vinyl benzoxazinanones with a variety of ketene intermediates via sequential visible-light photoactivation and palladium catalysis. It is well demonstrated that the traceless and transient generation of ketenes from α-diazoketones through visible-light-induced Wolff rearrangement is important for the success of present cycloaddition. Furthermore, chiral palladium catalysts with a new, chiral hybrid P, S ligand enable asymmetric cycloaddition with high reaction selectivity and enantiocontrol.
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