Asymmetric synthesis of functionalized cyclohexanes bearing five stereocenters via a one-pot organocatalytic Michael-Michael-1,2-addition sequence.
A highly stereoselective one-pot procedure involving an enantioselective Michael addition promoted by low loading of an amino-squaramide catalyst followed by an achiral base catalyzed domino Michael-Knoevenagel-type 1,2-addition sequence provides efficient access to fully substituted cyclohexanes bearing five contiguous stereogenic centers in good yields (68-86%) and excellent stereoselectivities (>30 : 1 dr and 96-99% ee).
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany. enders@rwth-aachen.de.
Pankaj
P
Chauhan
Gregor
G
Urbanietz
Gerhard
G
Raabe
Dieter
D
Enders
D002384:Catalysis; D018360:Crystallography, X-Ray; D003510:Cyclohexanes / Q000138:chemical synthesis*; D008958:Models, Molecular; D015394:Molecular Structure; D013141:Spiro Compounds / Q000138:chemical synthesis*; D013237:Stereoisomerism
D003510:Cyclohexanes; D013141:Spiro Compounds