| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1346083 | Tetrahedron: Asymmetry | 2012 | 4 Pages |
A practical synthesis for new chiral phosphino-carboxamide ligands has been accomplished. These ligands were effectively modified both on the amide moiety and the phosphine atom. Application of these ligands in the Pd-catalyzed allylic alkylation of (E)-1,3-diphenyl-2-propenyl acetate proceeded with excellent conversions and with ee’s of up to 92%. The use of a camphane based chiral auxiliary was found to be crucial for the asymmetric induction.
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2-(Diphenylphosphino)-N-((1S,2R,3S,4R)-3-ethoxy-4,7,7-trimethylbicyclo[2.2.1]heptan-2-yl)-N-ethylbenzamideC33H40NO2Pde > 99% (NMR)[α]D=+58.8[α]D=+58.8 (c 0.15, CHCl3)Source of chirality: (+)-camphorAbsolute configuration: (1S,2R,3S,4R)
N-((1S,2R,3S,4R)-3-Butoxy-4,7,7-trimethylbicyclo[2.2.1]heptan-2-yl)-N-butyl-2-(diphenylphosphino)benzamideC37H48NO2Pde = 99% (NMR)[α]D=+48.1[α]D=+48.1 (c 0.42, CHCl3)Source of chirality: (+)-camphorAbsolute configuration: (1S,2R,3S,4R)
N-Benzyl-N-((1S,2R,3S,4R)-3-(benzyloxy)-4,7,7-trimethylbicyclo[2.2.1]heptan-2-yl)-2-(diphenylphosphino)benzamideC43H44NO2Pde > 99% (NMR)[α]D=+156.0[α]D=+156.0 (c 0.35, CHCl3)Source of chirality: (+)-camphorAbsolute configuration: (1S,2R,3S,4R)
2-(Dicyclohexylphosphino)-N-((1S,2R,3S,4R)-3-ethoxy-4,7,7-trimethylbicyclo[2.2.1]heptan-2-yl)-N-ethylbenzamideC33H52NO2Pde > 99% (NMR)[α]D=+0.5[α]D=+0.5 (c 0.38, CHCl3)Source of chirality: (+)-camphorAbsolute configuration: (1S,2R,3S,4R)
2-(Diphenylphosphino)-N-isopropyl-N-((1S,2R,3S,4R)-3-methoxy-4,7,7-trimethylbicyclo[2.2.1]heptan-2-yl)benzamideC33H40NO2Pde > 99% (NMR)[α]D=-14.0[α]D=-14.0 (c 0.31, CHCl3)Source of chirality: (+)-camphorAbsolute configuration: (1S,2R,3S,4R)
2-(Diphenylphosphino)-N-((1S,2S,3R,4R)-3-ethoxy-4,7,7-trimethylbicyclo[2.2.1]heptan-2-yl)-N-ethylbenzamideC33H40NO2Pde > 99% (NMR)[α]D=-23.2[α]D=-23.2 (c 0.23, CHCl3)Source of chirality: (+)-camphorAbsolute configuration: (1S,2S,3R,4R)
2-(Diphenylphosphino)-N-ethyl-N-((1R,2R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl)benzamideC31H36NOPde > 99% (NMR)[α]D=+22.8[α]D=+22.8 (c 0.50, CHCl3)Source of chirality: (+)-camphorAbsolute configuration: (1R,2R,4R)
2-(Diphenylphosphino)-N-ethyl-N-((1R,2S,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl)benzamideC31H36NOPde > 99% (NMR)[α]D=-100.7[α]D=-100.7 (c 0.15, CHCl3)Source of chirality: (+)-camphorAbsolute configuration: (1R,2S,4R)
