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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
Author(s) -
Zhao Hongwu,
Yue Yuanyuan,
Li Hailong,
Sheng Zhihui,
Yang Zhao,
Meng Wei
Publication year - 2013
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201300090
Subject(s) - chemistry , enantiopure drug , enantioselective synthesis , chirality (physics) , axial chirality , axial symmetry , bipyridine , absolute configuration , stereochemistry , combinatorial chemistry , organic chemistry , catalysis , crystal structure , chiral symmetry breaking , symmetry breaking , physics , structural engineering , quantum mechanics , nambu–jona lasinio model , engineering
A series of novel axially chiral 2,2′‐bipyridine N , N′ ‐dioxides bearing C 1 or C 2 ‐symmetry have been synthesized by the use of enantiopure α ‐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.