| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1349507 | Tetrahedron: Asymmetry | 2006 | 9 Pages |
The synthesis of a number of novel chiral bis(oxazolyl) ligands with a biphenyl backbone from ellagic acid 1 and their application in the copper(I)-catalyzed asymmetric cyclopropanation was described.
Graphical abstractSynthesis of novel chiral ligands and their application in the copper(I)-catalyzed asymmetric cyclopropanation of styrene with ethyl diazoacetate.Figure optionsDownload full-size imageDownload as PowerPoint slide
(aR)-2,2′,3,3′,4,4′-Hexabenzyloxy-5,5′-dibenzyl-6,6′-diphenic acidC70H58O10[α]D = −66 (c 1 g/100 ml, CHCl3)Absolute configuration: (aR)
(aR)-2,2′,3,3′,4,4′-Hexabenzyloxy-5,5′-dibenzyl-6,6′-bis[N-(1,1-dimethyl-2-hydroxyethyl)carboxamido]-1,1′-biphenylC78H76N2O10[α]D = −19.6 (c 1 g/100 ml, CHCl3)Absolute configuration: (aR)
(aS)-2,2′,3,3′,4,4′-Hexabenzyloxy-5,5′-dibenzyl-6,6′-bis[N-(1S)-(1-iso-propyl-2-hydroxyethyl)carboxamido]-1,1′-biphenylC80H80N2O10[α]D = +1.5 (c 1 g/100 ml, CHCl3)Absolute configuration: (aS,S,S)
(aS)-2,2′,3,3′,4,4′-Hexabenzyloxy-5,5′-dibenzyl-6,6′-bis[N-(1S)-(1-tert-butyl-2-hydroxyethyl)carboxamido]-1,1′-biphenylC82H84N2O10[α]D = +16.5 (c 1 g/100 ml, CHCl3)Absolute configuration: (aS,S,S)
(aR)-2,2′,3,3′,4,4′-Hexabenzyloxy-5,5′-dibenzyl-6,6′-bis[N-(1S)-(1-iso-propyl-2-hydroxyethyl)carboxamido]-1,1′-biphenylC80H80N2O10[α]D = −45.8 (c 1 g/100 ml, CHCl3)Absolute configuration: (aR,S,S)
(aR)-2,2′,3,3′,4,4′-Hexabenzyloxy-5,5′-dibenzyl-6,6′-bis[N-(1S)-(1-tert-butyl-2-hydroxyethyl)carboxamido]-1,1′-biphenylC82H84N2O10[α]D = −57(c 1 g/100 ml, CHCl3)Absolute configuration: (aR,S,S)
(aR)-2,2′,3,3′,4,4′-Hexabenzyloxy-5,5′-dibenzyl-6,6′-bis(4,4-dimethyloxazolin-2-yl)-1,1′-biphenyl 9C78H72N2O8[α]D = +21.7 (c 1 g/100 ml, CHCl3)Absolute configuration: (aR)
(aS)-2,2′,3,3′,4,4′-Hexabenzyloxy-5,5′-dibenzyl-6,6′-bis[(4S)-(iso-propyloxazolin-2-yl)]-1,1′-biphenylC80H76N2O8[α]D = −51 (c 1 g/100 ml, CHCl3)Absolute configuration: (aS,S,S)
(aS)-2,2′,3,3′,4,4′-Hexabenzyloxy-5,5′-dibenzyl-6,6′-bis[(4S)-(tert-butyloxazolin-2-yl)]-1,1′-biphenylC82H80N2O8[α]D = −58 (c 1 g/100 ml, CHCl3)Absolute configuration: (aS,S,S)
(aR)-2,2′,3,3′,4,4′-Hexabenzyloxy-5,5′-dibenzyl-6,6′-bis[(4S)-(iso-propyloxazolin-2-yl)]-1,1′-biphenylC80H76N2O8[α]D = +35.5 (c 1 g/100 ml, CHCl3)Absolute configuration: (aR,S,S)
(aR)-2,2′,3,3′,4,4′-Hexabenzyloxy-5,5′-dibenzyl-6,6′-bis[(4S)-(tert-butyloxazolin-2-yl)]-1,1′-biphenylC82H80N2O8[α]D = +36.5 (c 1 g/100 ml, CHCl3)Absolute configuration: (aR,S,S)
