Synthesis, reaction, and recycle of fluorous palladium catalysts for an asymmetric allylic alkylation without using fluorous solvents.
[Chemical reaction: See text] Chiral fluorous aminophosphine 4c bearing two fluorous ponytails was prepared from (S)-prolinol and applied to palladium-catalyzed asymmetric allylic alkylation of 1,3-diphenyl-2-propenyl acetate (7) with a dialkyl malonate-BSA-LiOAc system with high enantioselectivities (up to 97% ee). Results indicated that the chiral fluorous palladium catalyst from ligand 4c was easily separated from the reaction mixture by simple solid/liquid separation and could be reused up to five times.
Mino
Takashi
T
Department of Applied Chemistry and Biotechnology, Faculty of Engineering, Chiba University, 1-33, Yayoi-cho, Inage-ku, Chiba 263-8522, Japan. tmino@faculty.chiba-u.jp
Sato
Yutaka
Y
Saito
Akio
A
Tanaka
Youichi
Y
Saotome
Hiroaki
H
Sakamoto
Masami
M
Fujita
Tsutomu
T