P-chiral o-phosphinophenol as a P/O hybrid ligand: preparation and use in Cu-catalyzed asymmetric conjugate addition of diethylzinc to acyclic enones.
[reaction: see text] (S)-2-(tert-Butylmethylphosphino)phenol and its methyl ether were synthesized from tert-butyldichlorophosphine via optically active phosphine-boranes as the intermediates. The former compound was used as a P/O hybrid ligand in the Cu-catalyzed asymmetric conjugate addition of diethylzinc to acyclic enones to achieve high enantioselectivity of up to 96%.
Takahashi
Yukitoshi
Y
Department of Chemistry, Faculty of Science, Chiba University, Inage-ku, Japan.
Yamamoto
Yoshikazu
Y
Katagiri
Kosuke
K
Danjo
Hiroshi
H
Yamaguchi
Kentaro
K
Imamoto
Tsuneo
T
D002384:Catalysis; D002599:Chalcone / Q000737:chemistry; D003300:Copper / Q000737:chemistry*; D008024:Ligands; D015394:Molecular Structure; D010100:Oxygen / Q000737:chemistry*; D010636:Phenols / Q000737:chemistry*; D010720:Phosphines / Q000737:chemistry*; D010758:Phosphorus / Q000737:chemistry*; D013237:Stereoisomerism; D015032:Zinc / Q000737:chemistry*
D008024:Ligands; D010636:Phenols; D010720:Phosphines; C510998:o-phosphinophenol; D010758:Phosphorus; D002599:Chalcone; D003300:Copper; C044646:phosphine; D015032:Zinc; D010100:Oxygen