Chua Pei Juan, Tan Bin, Zeng Xiaofei, Zhong Guofu
Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore, Singapore.
Bioorg Med Chem Lett. 2009 Jul 15;19(14):3915-8. doi: 10.1016/j.bmcl.2009.03.076. Epub 2009 Mar 25.
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%).
尽管许多手性胺，如L-脯氨酸及其衍生物，已被证明在许多反应中是多功能催化剂，但L-脯氨醇很少用作反应的有机催化剂。在此，我们报道了首例在苯甲酸存在下，L-脯氨醇催化环己酮与硝基烯烃的不对称迈克尔加成反应，得到具有高非对映选择性（87:13->99:1）和对映选择性（82-96%）的迈克尔加成产物。
