Chiral phosphine-free Pd-mediated asymmetric allylation of prochiral enolate with a chiral phase-transfer catalyst.
[reaction: see text]. A chiral phase-transfer catalyst has been applied to the asymmetric allylation of the tert-butyl glycinate-benzophenone Schiff base with various allylic acetates for the first time to give the allylated products in good yields and with comparable to higher enantioselectivity than for asymmetric alkylation at the same temperature (91-96% ee) without any chiral ligands for coordinating to the palladium.
Nakoji
M
M
Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501, Japan.
Kanayama
T
T
Okino
T
T
Takemoto
Y
Y
D000478:Alkylation; D000596:Amino Acids / Q000138:chemical synthesis; D002384:Catalysis; D005998:Glycine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D008024:Ligands; D010165:Palladium / Q000737:chemistry; D013237:Stereoisomerism
D000596:Amino Acids; D008024:Ligands; D010165:Palladium; C042193:glycine tert-butyl ester; D005998:Glycine