Pd-catalyzed asymmetric allylic amination of Morita-Baylis-Hillman adduct derivatives using chiral diaminophosphine oxides: DIAPHOXs.
[reaction: see text] Asymmetric allylic amination of allylic carbonates prepared from racemic Morita-Baylis-Hillman adducts proceeded in the presence of Pd catalyst, chiral diaminophosphine oxide (DIAPHOX), and BSA, affording the corresponding chiral aza-Morita-Baylis-Hillman adduct derivatives in excellent yield with up to 99% ee. The cyclic reaction products could be converted into various synthetically useful compounds such as chiral cyclic beta-amino acids.
Nemoto
Tetsuhiro
T
Graduate School of Pharmaceutical Sciences, Chiba University, Chiba 263-8522, Japan.
Fukuyama
Takashi
T
Yamamoto
Eri
E
Tamura
Shinji
S
Fukuda
Tomoaki
T
Matsumoto
Takayoshi
T
Akimoto
Yuichi
Y
Hamada
Yasumasa
Y
D002384:Catalysis; D015394:Molecular Structure; D010087:Oxides / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D010720:Phosphines / Q000737:chemistry*; D013237:Stereoisomerism
D010087:Oxides; D010720:Phosphines; D010165:Palladium