Core scaffold-inspired stereoselective synthesis of spiropyrazolones via an organocatalytic Michael/cyclization sequence.
Herein, the organocatalytic asymmetric Michael/cyclization sequence of α-isothiocyanato imides and esters with a variety of unsaturated pyrazolones is presented, in general, affording functionalized spiropyrazolones containing three contiguous stereogenic centers in high levels of diastereo- and enantioselectivity (up to 20:1 dr and 99% ee). Moreover, the current protocol provides a highly efficient and convenient strategy that allows rapid enantioselective construction of diversely spiropyrazolone skeletons with high optical purity.
Key Laboratory of Preclinical Study for New Drugs of Gansu Province, School of Basic Medical Sciences, Institute of Biochemistry and Molecular Biology, Lanzhou University, Lanzhou, China 730000.
Luping
L
Liu
Yuan
Y
Zhong
Panpan
P
Zhang
Xianxing
X
Jiang
Rui
R
Wang
D002384:Catalysis; D018360:Crystallography, X-Ray; D003500:Cyclization; D015394:Molecular Structure; D047069:Pyrazolones / Q000138:chemical synthesis* / Q000737:chemistry; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
D047069:Pyrazolones; D013141:Spiro Compounds