通过手性π-烯丙基钯催化剂进行对映选择性N-烯丙基化实现内消旋二酰胺衍生物的催化不对称去对称化：对映选择性的改进与反转

Catalytic asymmetric desymmetrization of meso-diamide derivatives through enantioselective N-allylation with a chiral pi-allyl Pd catalyst: improvement and reversal of the enantioselectivity.

作者信息

Kitagawa Osamu, Matsuo Shinichi, Yotsumoto Kanako, Taguchi Takeo

机构信息

Tokyo University of Pharmacy and Life Science, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan.

出版信息

J Org Chem. 2006 Mar 17;71(6):2524-7. doi: 10.1021/jo052488y.

DOI:10.1021/jo052488y

PMID:16526810

Abstract

In the presence of the Trost ligands-Pd catalysts, N-monoallylation of bis(2,4,6-triisopropylbenzne)sulfonylamides derived from meso-1,2-diamines proceeds with good to excellent enantioselectivity (85-96% ee) to give asymmetric desymmetrization products. Under the same conditions, in the reaction with meso-bistolunesulfonylamide derivatives, reversal of the enantioselectivity is observed.

摘要

在特罗斯特配体-钯催化剂存在下，由内消旋-1,2-二胺衍生的双（2,4,6-三异丙基苯）磺酰胺的N-单烯丙基化反应以良好至优异的对映选择性（85-96% ee）进行，生成不对称去对称化产物。在相同条件下，与内消旋双甲苯磺酰胺衍生物的反应中，观察到对映选择性的反转。