Copper-catalyzed enantioselective conjugate addition of Grignard reagent to non-activated acceptors

Xingchen Yan

Research output: ThesisThesis fully internal (DIV)

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Abstract

As a result of decades of research, it is currently possible to perform catalytic asymmetric conjugate additions of organometallics to many classes of Michael acceptors with excellent enantioselectivities and product yields. However, most of these examples comprise relatively reactive and conventional Michael acceptors. Conjugate additions to unconventional less reactive Michael acceptors such α,β-unsaturated carboxamides, α,β-unsaturated carboxylic acids and quinolines which are of major importance in organic synthesis, are still unreachable despite decades of research in this direction. To solve these long standing problems, we have developed a new strategy based on our previous researches. By combining reactive Lewis acids and Grignard reagents, we have tackled their reactivity issues and enabled their asymmetric conjugated addition reactions. Solving these problems allowed us to obtain a series of interesting chiral molecules that can be used for future transformations and applications.
Original languageEnglish
QualificationDoctor of Philosophy
Awarding Institution
  • University of Groningen
Supervisors/Advisors
  • Harutyunyan, Syuzanna, Supervisor
  • Browne, Wesley, Supervisor
Award date12-Jul-2019
Place of Publication[Groningen]
Publisher
Print ISBNs978-94-034-1746-2
Electronic ISBNs978-94-034-1745-5
Publication statusPublished - 2019

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