The asymmetric conjugate additions of aryl Grignard reagents to trisubstituted enones by chiral P,N ligand L6 with low catalyst loading(0.25–1.0 mol%)are disclosed.Chiral 2-ester chromanone and its analogs bearing a ...The asymmetric conjugate additions of aryl Grignard reagents to trisubstituted enones by chiral P,N ligand L6 with low catalyst loading(0.25–1.0 mol%)are disclosed.Chiral 2-ester chromanone and its analogs bearing a quaternary stereogenic centers at C2 position were produced in high to excellent yields,enantioselectivities and high turnover number.The notable features of this reaction include its broad substrate scope,complete 1,4-addition regioselectivities,applicability to both batch and flow for large scale synthesis.This report develops an efficient strategy to apply aryl Grignard reagents in asymmetric 1,4-conjugation reactions and provides a direct method to incorporate quaternary chiral centers toward the synthesis of biologically relevant chromanone derivatives.展开更多
The crystal structure of the new title compound 2,2-dimethyl-4-oxochroman-3-ylmorpholine-4-carbodithioate（C16H19NO3S2,Mr = 337.44） has been prepared and determined by single-crystal X-ray diffraction.The crystal is ...The crystal structure of the new title compound 2,2-dimethyl-4-oxochroman-3-ylmorpholine-4-carbodithioate（C16H19NO3S2,Mr = 337.44） has been prepared and determined by single-crystal X-ray diffraction.The crystal is of triclinic,space group P1 with a = 9.5518（7）,b = 9.7172（7）,c = 11.0220（8）,α = 67.08（1）,β = 74.66（1）,= 61.31（1）°,V = 822.72（10）3,Z = 2,Dc = 1.362 g/cm3,F（000） = 356,μ = 0.092 mm-1,MoKa radiation（λ = 0.71073）,R = 0.0515 and wR = 0.1389 for 2623 observed reflections with I 2（I）.X-ray diffraction analysis reveals that the chroman ring adopts a half-chair conformation while the morpholine ring shows a chair conformation.Intramolecular and intermolecular C–H···S and C–H···O hydrogen bonds together with π-π interations are found in the structure.The result of MTT assay shows the title compound displays good antiproliferative activity against two human cancer cell lines.展开更多
基金the financial support from the Sichuan Science and Technology Program(No.2022NSFSC0619)。
文摘The asymmetric conjugate additions of aryl Grignard reagents to trisubstituted enones by chiral P,N ligand L6 with low catalyst loading(0.25–1.0 mol%)are disclosed.Chiral 2-ester chromanone and its analogs bearing a quaternary stereogenic centers at C2 position were produced in high to excellent yields,enantioselectivities and high turnover number.The notable features of this reaction include its broad substrate scope,complete 1,4-addition regioselectivities,applicability to both batch and flow for large scale synthesis.This report develops an efficient strategy to apply aryl Grignard reagents in asymmetric 1,4-conjugation reactions and provides a direct method to incorporate quaternary chiral centers toward the synthesis of biologically relevant chromanone derivatives.
基金supported by the National Natural Science Foundation of China(No.21272086)China Postdoctoral Science Foundation(No.2012T50475)the Natural Science Foundation of Jiangsu Province(No.BK2011086)
文摘The crystal structure of the new title compound 2,2-dimethyl-4-oxochroman-3-ylmorpholine-4-carbodithioate（C16H19NO3S2,Mr = 337.44） has been prepared and determined by single-crystal X-ray diffraction.The crystal is of triclinic,space group P1 with a = 9.5518（7）,b = 9.7172（7）,c = 11.0220（8）,α = 67.08（1）,β = 74.66（1）,= 61.31（1）°,V = 822.72（10）3,Z = 2,Dc = 1.362 g/cm3,F（000） = 356,μ = 0.092 mm-1,MoKa radiation（λ = 0.71073）,R = 0.0515 and wR = 0.1389 for 2623 observed reflections with I 2（I）.X-ray diffraction analysis reveals that the chroman ring adopts a half-chair conformation while the morpholine ring shows a chair conformation.Intramolecular and intermolecular C–H···S and C–H···O hydrogen bonds together with π-π interations are found in the structure.The result of MTT assay shows the title compound displays good antiproliferative activity against two human cancer cell lines.
