Direct asymmetric Michael addition of thioether-based aryl sulfanyl-propan-2-one to nitroalkenes catalyzed by a chiral amine-thiourea bifunctional organocatalyst.
Although the organocatalytic direct asymmetric Michael reactions of carbonyl compounds to nitroalkenes have been investigated intensely, the Michael reaction of the thioether-based donors remains a rather undeveloped field. This work concerns the asymmetric Michael addition of aryl sulfanyl-propan-2-one to nitroalkenes with benzoic acid as an additive, and chiral amine-thiourea as a bifunctional organocatalyst. The reactions provided the highly functionalized chiral adducts with excellent enantioselectivities (up to 96% ee) and good yields. Moreover, the further transformed products exhibited excellent diastereoselectivity.
State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, China.
Xianxing
X
Jiang
Bangzhi
B
Zhang
Yifu
Y
Zhang
Li
L
Lin
Wenjin
W
Yan
Rui
R
Wang
D000096:Acetone / Q000737:chemistry*; D000475:Alkenes / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D013237:Stereoisomerism; D013440:Sulfides / Q000737:chemistry*; D013890:Thiourea / Q000737:chemistry*
D000475:Alkenes; D000588:Amines; D013440:Sulfides; D000096:Acetone; D013890:Thiourea