Asymmetric Allylic Substitutions Using Organometallic Reagents

Valentin Hornillos, Jean-Baptiste Gualtierotti, Ben L. Feringa*

*Corresponding author for this work

Research output: Chapter in Book/Report/Conference proceedingChapterAcademicpeer-review

33 Citations (Scopus)
178 Downloads (Pure)

Abstract

This chapter summarises recent progress in Cu-catalysed asymmetric allylic alkylation (AAA) with organometallic compounds, including Grignard, organolithium, organoaluminium, organozinc and organozirconium reagents. New reaction conditions and chiral ligands that improve these transformations or allow to overcome previous limitations associated with chemo-, regio- and enantioselectivities will be described. Moreover, a description of new ligands and conditions for the introduction of previously elusive nucleophiles, such as highly reactive organolithium compounds, is included together with a brief mechanistic discussion. Additionally, new challenging substrates which provide densely functionalised building blocks, as well as new synthetic applications that take advantage of the terminal olefin formed in these reactions, will be described.

Original languageEnglish
Title of host publicationPROGRESS IN ENANTIOSELECTIVE CU(I)-CATALYZED FORMATION OF STEREOGENIC CENTERS
Editors Harutyunyan
PublisherSpringer-Verlag Berlin Heidelberg
Pages1-39
Number of pages39
ISBN (Print)978-3-319-33412-7
DOIs
Publication statusPublished - 2016

Publication series

NameTopics in Organometallic Chemistry
PublisherSPRINGER-VERLAG BERLIN
Volume58
ISSN (Print)1436-6002

Keywords

  • Allylation
  • Asymmetric allylic substitution
  • Copper catalysis
  • Enantioselectivity
  • Organometallic reagents
  • CATALYZED ENANTIOSELECTIVE SYNTHESIS
  • QUATERNARY STEREOGENIC CENTERS
  • RING-CLOSING METATHESIS
  • GRIGNARD-REAGENTS
  • ORGANOLITHIUM REAGENTS
  • OXABICYCLIC ALKENES
  • CONJUGATE ADDITION
  • KINETIC RESOLUTION
  • VINYLALUMINUM REAGENTS
  • HYDROXYALKYL NHC

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