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Synthesis of Dendritic Schiff Base Ligands for Titanium Catalyzed Enantioselective HDA Reaction of Danishelfsky's Diene with Aldehydes
Author(s) -
Ji BaoMing,
Ding KuiLing,
Meng JiBen
Publication year - 2003
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.20030210705
Subject(s) - chemistry , schiff base , diene , enantioselective synthesis , catalysis , dendrimer , ligand (biochemistry) , titanium , pyran , medicinal chemistry , combinatorial chemistry , polymer chemistry , stereochemistry , organic chemistry , receptor , biochemistry , natural rubber
A new type of dendritic NOBIN derived Schiff base ligands has been synthesized and applied to titanium catalyzed hetero‐Diels‐Alder reaction of Danishelfsky's diene and aldehydes, affording the corresponding 2‐substituted 2,3‐dihydro‐4 H ‐pyran‐4‐one in good yields and moderate enantioselectivities (up to 59.2% ee ). It was found that the size of dendron attached to the tri‐dentated ligands has slight impact on the enantioselectivity of the reaction and the second generation of dendritic ligand exhibited the best enantioselectivity.