Amination of N-aryl prolinol via ring expansion and contraction: application to the chiral ligand for the catalytic asymmetric reaction.
Chiral diaminophosphines 4 were prepared from (S)-prolinol-derived aminophosphine oxide 5 by bromination with ring expansion followed by amination with ring contraction and reduction, using trichlorosilane. In the presence of 4 as a ligand, palladium-catalyzed asymmetric allylic alkylation of 1,3-diphenyl-2-propenyl acetate (11) with a dialkyl malonate-BSA-LiOAc system was successfully carried out with good enantioselectivities (up to 98% ee).
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
Saito
Akio
A
Tanaka
Youichi
Y
Hasegawa
Shintaro
S
Sato
Yutaka
Y
Sakamoto
Masami
M
Fujita
Tsutomu
T
D000586:Amination; D001555:Benzene Derivatives / Q000138:chemical synthesis / Q000737:chemistry; D002384:Catalysis; D008024:Ligands; D008968:Molecular Conformation; D015394:Molecular Structure; D011759:Pyrrolidines / Q000138:chemical synthesis / Q000737:chemistry
D001555:Benzene Derivatives; D008024:Ligands; D011759:Pyrrolidines; C010509:prolinol