A new powerful strategy for the organocatalytic asymmetric construction of a quaternary carbon stereogenic center.
A new method for chiral diamine-catalyzed Robinson-type annulation was developed to construct cyclohexenone derivatives bearing a quaternary carbon stereogenic center at the 4-position in high enantiomeric excess. This method was successfully applied to the short synthesis of (+)-sporochnol A.
Inokoishi
Yogo
Y
Laboratory of Natural Product Chemistry, Faculty of Science, Kochi University, Akebono-cho, Kochi 780-8520, Japan.
Sasakura
Niiha
N
Nakano
Keiji
K
Ichikawa
Yoshiyasu
Y
Kotsuki
Hiyoshizo
H
D000475:Alkenes / Q000138:chemical synthesis / Q000737:chemistry; D002244:Carbon / Q000737:chemistry*; D002384:Catalysis; D003512:Cyclohexanones / Q000138:chemical synthesis* / Q000737:chemistry; D003959:Diamines / Q000737:chemistry*; D015394:Molecular Structure; D010636:Phenols / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
D000475:Alkenes; D003512:Cyclohexanones; D003959:Diamines; D010636:Phenols; C445786:sporochnol A; D002244:Carbon