Role of ortho-substituents on rhodium-catalyzed asymmetric synthesis of β-lactones by intramolecular C-H insertions of aryldiazoacetates.
A rhodium-catalyzed asymmetric synthesis of β-lactones via intramolecular C-H insertion into the ester group of aryldiazoacetates has been developed. The β-lactones were synthesized in high yields and with high levels of diastereo- and enantioselectivity. Halo and trifluoromethyl substituents at the ortho position of the aryldiazoacetates enhance intramolecular C-H insertions over intermolecular reactions, allowing C-H insertion of even methyl C-H bonds.
Department of Chemistry, Emory University , 1515 Dickey Drive, Atlanta, Georgia 30322, United States.
Liangbing
L
Fu
Hengbin
H
Wang
Huw M L
HM
Davies
D001391:Azo Compounds / Q000737:chemistry*; D002384:Catalysis; D006860:Hydrogen Bonding; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism
D001391:Azo Compounds; D007783:Lactones; D012238:Rhodium