Organocatalytic asymmetric tandem Michael-Henry reactions: a highly stereoselective synthesis of multifunctionalized cyclohexanes with two quaternary stereocenters.
A novel organocatalytic asymmetric tandem Michael-Henry reaction catalyzed by 9-amino-9-deoxyepiquinine (VI) has been developed. The reaction was efficiently catalyzed by catalyst VI to give highly functionalized cyclohexanes with four stereogenic carbons including two quaternary stereocenters in excellent enantioselectivities (97 to >99% ee) and high diastereoselectivities (93:7-99:1 dr). Thus, the first organocatalytic asymmetric Henry reaction of common ketones as acceptors is shown.
Tan
Bin
B
Division of Chemistry & Biological Chemistry, School of Physical and Mathamatical Sciences, Nanyang Technological University, Singapore, Singapore.
Chua
Pei Juan
PJ
Li
Yongxin
Y
Zhong
Guofu
G
D002384:Catalysis; D003510:Cyclohexanes / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D011807:Quinolizines / Q000737:chemistry*; D013237:Stereoisomerism
C517737:9-amino-9-deoxyepiquinine; D003510:Cyclohexanes; D007659:Ketones; D011807:Quinolizines