Rhodium(I)-catalyzed asymmetric addition of organometallic reagents to unsaturated compounds

Hsyueh Liang Wu, Ping Yu Wu

Research output: Chapter in Book/Report/Conference proceedingChapter

Abstract

The rhodium-catalyzed asymmetric addition reaction of organoboron reagents to a,ß-unsaturated compounds has seen significant growth in the past two decades for their user-friendly reaction conditions, which generally allow the use of water as a cosolvent. This chapter highlights advancements ranging from 2004 to 2017 in this field and organizes the content in terms of the applicable substrates with respect to the chiral ligands. Bis-sulfoxide ligands emerged as one of the privileged ligand family in C-H oxidation reaction by coordinating Pd with sulfur atoms. Ligands with two distinct chelating centers are regarded as hybrid ligands. While dienes generally display greater catalytic activity than phosphorus ligands, the coordinating ability of diene ligands is weaker than that of phosphine-based ones. a,ß-unsaturated esters are generally good reaction partners in the Rh-catalyzed conjugate addition reactions for 1,4-addition products. Nitroolefin compounds are excellent substrates in the rhodium-catalyzed asymmetric conjugate addition reactions as a result of their highly electrophilic nature.

Original languageEnglish
Title of host publicationRhodium Catalysis in Organic Synthesis
Subtitle of host publicationMethods and Reactions
Publisherwiley
Pages85-116
Number of pages32
ISBN (Electronic)9783527811878
ISBN (Print)9783527343645
DOIs
Publication statusPublished - 2018 Dec 28

Keywords

  • Bis-sulfoxide ligands
  • chiral ligands
  • diene ligands
  • hybrid ligands
  • nitroolefin compounds
  • rhodium-catalyzed asymmetric addition reaction
  • unsaturated esters

ASJC Scopus subject areas

  • Chemistry(all)

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