Chiral bis(imidazolinyl)phenyl NCN pincer rhodium(III) catalysts for enantioselective allylation of aldehydes and carbonyl-ene reaction of trifluoropyruvates.
Chiral NCN pincer rhodium(III) complexes with bis(imidazolinyl)phenyl ligands were found to be effective catalysts for the allylation of a variety of electronically and structurally diverse aldehydes with allyltributyltin, giving the corresponding optically active homoallylic alcohols in high yields with enantioselectivities of up to 97% ee. These complexes were also applied in the carbonyl-ene reaction of ethyl or methyl trifluoropyruvate with various 2-arylpropenes. With the aid of silver trifluoromethanesulfonate, the pincer rhodium(III) catalysts could catalyze the reaction to provide the corresponding chiral α-hydroxy-α-trifluoromethyl esters in good yields with high stereoselectivities (up to 95% ee).
Henan Key Laboratory of Chemical Biology and Organic Chemistry, The College of Chemistry and Molecular Engineering, Zhengzhou University , Zhengzhou 450052, People's Republic of China.
Tao
T
Wang
Xin-Qi
XQ
Hao
Juan-Juan
JJ
Huang
Jun-Long
JL
Niu
Jun-Fang
JF
Gong
Mao-Ping
MP
Song
D000447:Aldehydes / Q000737:chemistry*; D000498:Allyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D056831:Coordination Complexes / Q000737:chemistry*; D048288:Imidazolines / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D019289:Pyruvic Acid / Q000031:analogs & derivatives / Q000737:chemistry*; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism
D000447:Aldehydes; D000498:Allyl Compounds; D056831:Coordination Complexes; D048288:Imidazolines; D009942:Organometallic Compounds; D019289:Pyruvic Acid; D012238:Rhodium