Overcoming the Naphthyl Requirement in Stereospecific Cross-Couplings to Form Quaternary Stereocenters

Overcoming the Naphthyl Requirement in Stereospecific Cross-Couplings to Form Quaternary Stereocenters

The use of a simple stilbene ligand has enabled a stereospecific Suzuki–Miyaura cross-coupling of tertiary benzylic carboxylates, including those lacking naphthyl substituents. This method installs challenging all-carbon diaryl quaternary stereocenters in good yield and ee and represents an importan...

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Veröffentlicht in:Journal of the American Chemical Society 2021-06, Vol.143 (23), p.8608-8613
Hauptverfasser: Xu, Jianyu, Bercher, Olivia P, Watson, Mary P
Format: Artikel
Sprache:eng
Schlagworte:
Carboxylic Acids - chemistry
Ligands
Molecular Structure
Naphthalenes - chemistry
Stereoisomerism
Stilbenes - chemistry
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Zusammenfassung:The use of a simple stilbene ligand has enabled a stereospecific Suzuki–Miyaura cross-coupling of tertiary benzylic carboxylates, including those lacking naphthyl substituents. This method installs challenging all-carbon diaryl quaternary stereocenters in good yield and ee and represents an important breakthrough in the “naphthyl requirement” that pervades stereospecific cross-couplings involving enantioenriched electrophiles.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.1c03898