Stereochemistry of the asymmetric carbopalladation of allenes followed by nucleophilic substitution reactions with carbo- and aminonucleophiles.
The stereochemistry of the asymmetric palladium-catalyzed reaction of allenes with iodobenzene followed by nucleophilic substitution reaction with sodium malonate and N-methylbenzylamine is described. On the basis of the absolute configuration of the product and the stereochemical result of a similar reaction of a chiral allene, the mechanism of the above asymmetric reactions is discussed.
Kato
Fumiko
F
Tohoku Pharmaceutical University, 4-4-1 Komatsushima, Aoba-ku, Sendai, Miyagi 981-8558, Japan.
Hiroi
Kunio
K
D000466:Alkadienes / Q000737:chemistry*; D002384:Catalysis; D002851:Chromatography, High Pressure Liquid; D002855:Chromatography, Thin Layer; D007202:Indicators and Reagents; D007462:Iodobenzenes; D008024:Ligands; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008968:Molecular Conformation; D009942:Organometallic Compounds / Q000737:chemistry*; D010084:Oxidation-Reduction; D010165:Palladium / Q000737:chemistry*; D013055:Spectrophotometry, Infrared; D013237:Stereoisomerism; D013816:Thermodynamics
D000466:Alkadienes; D007202:Indicators and Reagents; D007462:Iodobenzenes; D008024:Ligands; D009942:Organometallic Compounds; C025947:propadiene; D010165:Palladium; C031905:iodobenzene