Enantioselective annulation reactions: from fischer indolization to de novo arene Construction

By: Contributor(s): Material type: TextTextLanguage: en. Publication details: Bengaluru : Indian Institute of science , 2022.Description: iv, 256p. e-Thesis col. ill. ; 29.1cm * 20.5cm 20.12MbSubject(s): DDC classification:
  • 547 GHO
Online resources: Dissertation note: PhD; 2022; Organic chemistry Summary: In summary, we have developed the first decarboxylative [4+2]-annulation of ethynyl benzoxazinanones with azlactones for the enantioselective synthesis of cyclic α-quaternary α-acylaminoamides.25 This direct and modular approach combines dipolar copper-allenylidene intermediates and enolates generated from azlactones under bifunctional tertiary aminourea catalysis in a cooperative fashion. The resulting 3,4-dihydroquinolin-2-ones 3.43, bearing vicinal tertiary and quaternary stereogenic centers , are formed as a single diastereomer with good to excellent enantioselectivity. The products are densely functionalized and the synthetic versatility of the terminal alkyne group is demonstrated through a number of synthetic elaborations. This reaction represents the first direct catalytic enantioselective route to cyclic α-quaternary α-acylaminoamides
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Includes bibliographical references and index

PhD; 2022; Organic chemistry

In summary, we have developed the first decarboxylative [4+2]-annulation of ethynyl benzoxazinanones with azlactones for the enantioselective synthesis of cyclic α-quaternary α-acylaminoamides.25 This direct and modular approach combines dipolar copper-allenylidene intermediates and enolates generated from azlactones under bifunctional tertiary aminourea catalysis in a cooperative fashion. The resulting 3,4-dihydroquinolin-2-ones 3.43, bearing vicinal tertiary and quaternary stereogenic centers , are formed as a single diastereomer with good to excellent enantioselectivity. The products are densely functionalized and the synthetic versatility of the terminal alkyne group is demonstrated through a number of synthetic elaborations. This reaction represents the first direct catalytic enantioselective route to cyclic α-quaternary α-acylaminoamides

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