Highly enantioselective hydrogenation of alpha-arylmethylene cycloalkanones catalyzed by iridium complexes of chiral spiro aminophosphine ligands.
The highly efficient asymmetric hydrogenation of alpha-arylmethylene cycloalkanones catalyzed by Ir-complexes of chiral spiro aminophosphine ligands was developed, providing chiral exo-cyclic allylic alcohols at high yields with excellent enantioselectivities (up to 97% ee) and high turnover numbers (S/C up to 10,000). This new reaction provided an efficient method for the synthesis of the key intermediate of the active form of the anti-inflammatory loxoprofen.
Xie
Jian-Bo
JB
State Key Laboratory and Institute of Elemento-organic Chemistry, Nankai University, Tianjin 300071, China.
Xie
Jian-Hua
JH
Liu
Xiao-Yan
XY
Kong
Wei-Ling
WL
Li
Shen
S
Zhou
Qi-Lin
QL
D000438:Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D006865:Hydrogenation; D007495:Iridium / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D008024:Ligands; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D010720:Phosphines / Q000737:chemistry*; D013141:Spiro Compounds / Q000737:chemistry*; D013237:Stereoisomerism
D000438:Alcohols; D007659:Ketones; D008024:Ligands; D009942:Organometallic Compounds; D010720:Phosphines; D013141:Spiro Compounds; D007495:Iridium