A novel class of P-O monophosphite ligands derived from D-mannitol: broad applications in highly enantioselective Rh-catalyzed hydrogenations.
We report on a new class of P-O monophosphite ligands (designated 3a-k) with a double six-membered-ring backbone onto which are attached additional groups and on applications of their Rh complexes in the hydrogenation of enamides, alpha-dehydroamino acid esters, dimethyl itaconate, and beta-(acylamino)acrylates. Our results demonstrate that the Rh complexes with ligands 3a-k exhibit high enantioselectivity and reactivity in asymmetric hydrogenation reactions. An ee value of up to 98.0% was obtained for the hydrogenation of alpha-dehydroamino acid esters, and the ee values were all over 99% for the other three types of substrate, with a turnover number of up to 5000.
Huang
Hanmin
H
Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, PR China.
Zheng
Zhuo
Z
Luo
Huili
H
Bai
Changmin
C
Hu
Xinquan
X
Chen
Huilin
H
D002384:Catalysis; D006865:Hydrogenation; D007202:Indicators and Reagents; D008024:Ligands; D008353:Mannitol / Q000737:chemistry*; D015394:Molecular Structure; D009943:Organophosphorus Compounds / Q000032:analysis / Q000138:chemical synthesis* / Q000737:chemistry*; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism
D007202:Indicators and Reagents; D008024:Ligands; D009943:Organophosphorus Compounds; D008353:Mannitol; D012238:Rhodium