L-prolinol as a highly enantioselective catalyst for Michael addition of cyclohexanone to nitroolefins.
Though many chiral amines such as l-proline and its derivatives have proven to be versatile catalysts in many reactions, L-prolinol was seldom used as organocatalyst for reactions. Herein, we report the first L-prolinol catalyzed asymmetric Michael addition of cyclohexanone to nitroolefins in the presence of benzoic acid to afford Michael adducts with high diastereoselectivities (87:13->99:1) and enantioselectivities (82-96%).
Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore, Singapore.
Pei Juan
PJ
Chua
Bin
B
Tan
Xiaofei
X
Zeng
Guofu
G
Zhong
D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry; D019817:Benzoic Acid / Q000737:chemistry; D002384:Catalysis; D003512:Cyclohexanones / Q000737:chemistry*; D011759:Pyrrolidines / Q000737:chemistry*; D013237:Stereoisomerism; D013696:Temperature
D000475:Alkenes; D003512:Cyclohexanones; D011759:Pyrrolidines; C010509:prolinol; C036468:cyclohexanone; D019817:Benzoic Acid