Direct organocatalytic asymmetric aldol reaction of alpha-isothiocyanato imides to alpha-ketoesters under low ligand loading: a doubly stereocontrolled approach to cyclic thiocarbamates bearing chiral quaternary stereocenters.
The first doubly stereocontrolled organocatalytic asymmetric aldol reaction of alpha-isothiocyanato imides with alpha-ketoesters by using rosin-derived tertiary amine-thiourea under low ligand loading to form cyclic thiocarbamates bearing quaternary stereogenic centers with high levels of enantio- and diastereoselectivity (up to 99% ee, and 97:3 dr) is presented. This reaction provides a convenient doubly stereocontrolled method to access synthetic useful multiply substituted cyclic thiocarbamates with high optical purity.
Jiang
Xianxing
X
State Key Laboratory of Applied Organic Chemistry, Institute of Biochemistry and Molecular Biology, Key Laboratory of Preclinical Study for New Drugs of Gansu Province, Lanzhou University, Lanzhou, 730000, China.
Zhang
Gen
G
Fu
Dan
D
Cao
Yiming
Y
Shen
Fangfang
F
Wang
Rui
R
D003500:Cyclization; D007094:Imides / Q000737:chemistry*; D017879:Isothiocyanates / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D008024:Ligands; D015394:Molecular Structure; D013237:Stereoisomerism; D013859:Thiocarbamates / Q000138:chemical synthesis* / Q000737:chemistry
D007094:Imides; D017879:Isothiocyanates; D007659:Ketones; D008024:Ligands; D013859:Thiocarbamates