Asymmetric Synthesis of Novel Axially Chiral 2,2＇-Bipyridine N,N＇-Dioxides Bearing α-Amino Acid Residues and Their Applications in Enantioselective Allylation of Aromatic Aldehydes with Allyltrichlorosilane  

Asymmetric Synthesis of Novel Axially Chiral 2,2＇-Bipyridine N,N＇-Dioxides Bearing a-Amino Acid Residues and Their Applications in Enantioselective Allylation of Aromatic Aldehydes with Allyltrichlorosilane

作　　者：Hongwu Zhao Yuanyuan Yue Hailong Li Zhihui Sheng Zhao Yang Wei Meng 

机构地区：[1]College of Life Science and Bio-engineering, Beijing University of Technology, Beijing 100124, China

出　　处：《Chinese Journal of Chemistry》2013年第4期485-493,共9页中国化学（英文版）

基　　金：We thank Beijing Municipal Commission of Edu- cation （No. JC015001200902）, Beijing Municipal Natu- ral Science Foundation （Nos. 710201, 2122008）, Basic Research Foundation of Beijing University of Technol- ogy （X40 15001201101）, Funding Project for Academic Human Resources Development in Institutions ofHigher Learning Under the Jurisdiction of Beijing Municipality （No. PHR201008025）, Doctoral Scientific Research Start-up Foundation of Beijing University of Technology （No. 52015001200701） for financial sup- ports.

摘　　要：A series of novel axially chiral 2,2＇-bipyridine N,N＇-dioxides bearing C1 or C2-symmetry have been synthesized by the use of enantiopure a-amino acids as chiral sources. The absolute stereochemistry of the axial chirality of these organocatalysts has been clearly assigned by means of CD measurements together with literature protocols. The reactivities and enantioselectivities of these organocatalysts have been examined in the reactions of aromatic aldehydes with allyltrichlorosilane, thus providing the desired products with moderate yields and enantioselectivies.A series of novel axially chiral 2,2＇-bipyridine N,N＇-dioxides bearing C1 or C2-symmetry have been synthesized by the use of enantiopure a-amino acids as chiral sources. The absolute stereochemistry of the axial chirality of these organocatalysts has been clearly assigned by means of CD measurements together with literature protocols. The reactivities and enantioselectivities of these organocatalysts have been examined in the reactions of aromatic aldehydes with allyltrichlorosilane, thus providing the desired products with moderate yields and enantioselectivies.

关 键 词：2 2＇-bipyridine N N＇-dioxide organocatalyst asymmetric catalysis enantioselective allylation allyl-trichlorosilane 

分 类 号：O621.34[理学—有机化学] O623.412.1[理学—化学]