Efficient direct asymmetric vinylogous Michael addition reactions of gamma-butenolides to chalcones catalyzed by vicinal primary-diamine salts.
The first direct organocatalytic asymmetric vinylogous Michael addition reactions of gamma-butenolides to chalcones have been developed by using chiral 1,2-diaminocyclohexane as a novel organocatalyst via a di-iminium transition state to provide syn-Michael products with good yields, high diastereoselectivities and enantioselectivities (up to 78% yield, >99 : 1 dr and 96% ee).
Wang
Junfeng
J
State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, 38 Xueyuan Road, Beijing, 100191, P. R. China.
Qi
Chao
C
Ge
Zemei
Z
Cheng
Tieming
T
Li
Runtao
R
D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000737:chemistry; D002384:Catalysis; D047188:Chalcones / Q000737:chemistry*; D018360:Crystallography, X-Ray; D008958:Models, Molecular; D013237:Stereoisomerism
D047188:Chalcones; C004511:butenolide; D015107:4-Butyrolactone