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pd_meltingpoint:89°C
Purity:99%
|
Synthesis Reference(s) |
Journal of the American Chemical Society, 78, p. 4942, 1956 DOI: 10.1021/ja01600a035 |
InChI:InChI=1/C15H14O2/c16-15(17)14(13-9-5-2-6-10-13)11-12-7-3-1-4-8-12/h1-10,14H,11H2,(H,16,17)
Enantioselective hydrogenations of α,β-u...
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2,3-diphenylacrylic acid
(2S)-2,3-diphenylpropanoic acid
(R)-2,3-diphenylpropanoic acid
| Conditions | Yield |
|---|---|
|
With
bis(norbornadiene)rhodium(l)tetrafluoroborate; (S(p),S(p))-2,2''-bis(diphenylphosphino)-1,1''-biferrocene; hydrogen;
In
methanol;
at 25 ℃;
for 14.5h;
under 60006 Torr;
optical yield given as %ee;
enantioselective reaction;
Autoclave;
|
|
|
With
5% Pd(II)/C(eggshell); Cinchonidin;
In
1,4-dioxane; water;
at 22.84 ℃;
optical yield given as %ee;
enantioselective reaction;
Kinetics;
|
|
|
With
5% Pd(II)/C(eggshell); Cinchonin;
In
1,4-dioxane; water;
at 22.84 ℃;
optical yield given as %ee;
enantioselective reaction;
Kinetics;
|
|
|
With
5% Pd(II)/C(eggshell); hydrogen; cinchonidine; benzylamine;
In
1,4-dioxane; water;
at 49.84 ℃;
optical yield given as %ee;
enantioselective reaction;
|
|
|
With
5%-palladium/activated carbon; hydrogen; cinchonine;
In
1,4-dioxane; water;
at 23 ℃;
under 1500.15 Torr;
optical yield given as %ee;
enantioselective reaction;
|
|
|
With
palladium on activated charcoal; hydrogen; cinchonidine; benzylamine;
In
1,4-dioxane;
at 22.84 ℃;
under 7500.75 Torr;
Overall yield = 100%; Optical yield = 82%ee; enantioselective reaction;
|
|
|
With
cinchonidine; 5% Pd/CNT; hydrogen; benzylamine;
In
1,4-dioxane; water;
under 750.075 Torr;
Reagent/catalyst;
enantioselective reaction;
Catalytic behavior;
|
75 % ee |
|
With
bis(norbornadiene)rhodium(l)tetrafluoroborate; (R)-1-[2-(2'-diphenylphosphinophenyl)-ferrocenyl]ethyldi[bis-(3,5-trifluoromethyl)phenyl]phosphine; hydrogen;
In
methanol;
at 20 ℃;
for 19h;
under 37503.8 Torr;
Inert atmosphere;
Autoclave;
|
82% ee |
|
With
bis(norbornadiene)rhodium(l)tetrafluoroborate; (Sp)-2-{(R)-1-bis[3,5-bis(trifluoromethyl)phenyl]phosphinoethyl}-(Sp)-2″-diphenylphosphino-1,1″-biferrocene; hydrogen;
In
methanol;
at 20 ℃;
for 19h;
under 37503.8 Torr;
Inert atmosphere;
Autoclave;
|
80% ee |
|
With
hydrogen; benzylamine;
In
1,4-dioxane; water;
at 22.84 ℃;
under 760.051 Torr;
enantioselective reaction;
|
80 % ee |
|
With
5%-palladium/activated carbon; hydrogen; benzylamine; Cinchonidin;
In
1,4-dioxane; water;
at 22.84 ℃;
Reagent/catalyst;
enantioselective reaction;
|
58 % ee |
(E)-2,3-diphenylpropenoic acid
(2S)-2,3-diphenylpropanoic acid
(R)-2,3-diphenylpropanoic acid
| Conditions | Yield |
|---|---|
|
With
hydrogen; Cinchonidin;
In
water; N,N-dimethyl-formamide;
at 24.9 ℃;
Product distribution;
conversion dependence of the optical yield;
|
|
|
With
hydrogen;
cinchonidine;
In
methanol;
at 24.9 ℃;
for 0.333333h;
under 760 Torr;
Product distribution;
variation of cinchona alkaloids on Pd/TiO2 catalyst and solvent;
|
|
|
With
hydrogen;
cinchonidine;
In
water; N,N-dimethyl-formamide;
at 24.9 ℃;
under 760 Torr;
|
|
|
With
hydrogen;
diacetato[(R)-(+)-2,2'-bis(diphenylphosphino)-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl]ruthenium(II);
In
methanol;
at 60 ℃;
for 61h;
under 20520 Torr;
Yield given. Yields of byproduct given. Title compound not separated from byproducts;
|
|
|
With
hydrogen; benzylamine;
chinchonidine-modified Pd;
In
1,4-dioxane; water;
at 24.85 ℃;
under 750.06 Torr;
|
|
|
With
hydrogen;
palladium;
In
1,4-dioxane; water;
at 24.85 ℃;
|
|
|
With
hydrogen;
cinchonidine-modified Pd;
In
1,4-dioxane; water;
at 19.85 ℃;
under 0.1 Torr;
Further Variations:;
Pressures;
Product distribution;
|
|
|
With
hydrogen;
[Rh(cycloocta-1,5-diene){(S,S,S)-dipof}]CF3SO3;
In
methanol;
at 39.85 ℃;
for 24h;
under 15001.2 Torr;
Further Variations:;
Catalysts;
Product distribution;
|
|
|
With
hydrogen; benzylamine; Cinchonidin;
palladium;
In
1,4-dioxane; water;
at 22 - 24 ℃;
Further Variations:;
Reagents;
Product distribution;
atmospheric pressure;
|
|
|
With
bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; phosphoramidite based on chiral-3,3'-dimethylbinol; hydrogen;
tris-(o-tolyl)phosphine;
In
water; isopropyl alcohol;
at 60 ℃;
for 16h;
under 18751.5 Torr;
Title compound not separated from byproducts;
|
|
|
With
5%-palladium/activated carbon; hydrogen; cinchonidine; benzylamine;
In
1,4-dioxane; water;
at 23 ℃;
under 760.051 Torr;
optical yield given as %ee;
enantioselective reaction;
|
|
|
With
palladium/alumina; hydrogen; benzylamine; (8R,9S)-cinchonine;
In
water; N,N-dimethyl-formamide;
at -0.16 ℃;
under 750.075 Torr;
optical yield given as %ee;
|
|
|
With
10% Pd/Al2O3; hydrogen; cinchonidine; benzylamine;
In
water; N,N-dimethyl-formamide;
at 24.84 ℃;
under 750.075 Torr;
optical yield given as %ee;
enantioselective reaction;
|
|
|
With
10% Pd/Al2O3; hydrogen; cinchonine; benzylamine;
In
water; N,N-dimethyl-formamide;
at 24.84 ℃;
under 750.075 Torr;
optical yield given as %ee;
enantioselective reaction;
|
|
|
With
5% Pd/Al2O3; hydrogen; cinchonidine; benzylamine;
In
water; N,N-dimethyl-formamide;
at 1.84 ℃;
under 750.075 Torr;
optical yield given as %ee;
enantioselective reaction;
|
|
|
With
C51H54IrNOP; hydrogen; caesium carbonate;
In
methanol;
at 45 ℃;
for 12h;
under 4560.31 Torr;
optical yield given as %ee;
enantioselective reaction;
|
|
|
With
bis(norbornadiene)rhodium(l)tetrafluoroborate; (S)-1-{(SFc)-2-[2-(diphenylphosphino)phenyl]ferrocenyl}ethylbis[3,5-bis-(trifluoromethyl)phenyl]phosphine; hydrogen;
In
methanol;
at 20 ℃;
for 19h;
under 38002.6 Torr;
Reagent/catalyst;
Autoclave;
|
89 % ee |
|
Multi-step reaction with 4 steps
1: thionyl chloride / 4 - 42 °C
2: diisobutylaluminium hydride / tetrahydrofuran / 2 h / -70 - -10 °C
3: Dess-Martin periodane / dichloromethane / 2.5 h / -10 °C
4: aldehyde dehydrogenase from bovine lens; NADH; ene-reductase from Gluconobacter oxydans / aq. phosphate buffer / 30 °C / pH 7 / Enzymatic reaction
With
thionyl chloride; aldehyde dehydrogenase from bovine lens; ene-reductase from Gluconobacter oxydans; diisobutylaluminium hydride; Dess-Martin periodane; NADH;
In
tetrahydrofuran; aq. phosphate buffer; dichloromethane;
|
|
|
Multi-step reaction with 4 steps
1: thionyl chloride / 4 - 42 °C
2: diisobutylaluminium hydride / tetrahydrofuran / 2 h / -70 - -10 °C
3: Dess-Martin periodane / dichloromethane / 2.5 h / -10 °C
4: aldehyde dehydrogenase from bovine lens; NADH; ene-reductase from Bacillus subtilis / aq. phosphate buffer / 30 °C / pH 7 / Enzymatic reaction
With
thionyl chloride; aldehyde dehydrogenase from bovine lens; ene-reductase from Bacillus subtilis; diisobutylaluminium hydride; Dess-Martin periodane; NADH;
In
tetrahydrofuran; aq. phosphate buffer; dichloromethane;
|
|
|
With
5%-palladium/activated carbon; hydrogen; benzylamine; Cinchonidin;
In
1,4-dioxane; water;
at 22.84 ℃;
|
83 % ee |
|
With
4.92 % Pd/C; hydrogen; cinchonidine; benzylamine;
In
1,4-dioxane;
at 23 ℃;
Reagent/catalyst;
Optical yield = 70 %ee; enantioselective reaction;
|
|
|
With
hydrogen;
at -0.16 ℃;
Temperature;
Optical yield = 80 %ee; enantioselective reaction;
|
|
|
(E)-2,3-diphenylpropenoic acid;
With
5%-palladium/activated carbon; hydrogen; benzylamine; Cinchonidin;
In
1,4-dioxane; water;
at 22.84 - 79.84 ℃;
for 2h;
under 750.075 Torr;
With
hydrogenchloride;
In
water;
enantioselective reaction;
|
82 % ee |
|
(E)-2,3-diphenylpropenoic acid;
With
5%-palladium/activated carbon; hydrogen; benzylamine; (+)-cinchonine;
In
1,4-dioxane; water;
at 22.84 ℃;
under 750.075 Torr;
With
hydrogenchloride;
enantioselective reaction;
|
54 % ee |
|
With
hydrogen; benzylamine;
In
1,4-dioxane; water;
at 20 ℃;
for 2h;
under 76.0051 Torr;
Overall yield = 49.8 %; enantioselective reaction;
|
17 % ee |
|
With
hydrogen; benzylamine;
In
1,4-dioxane; water;
at 20 ℃;
for 2h;
under 76.0051 Torr;
Overall yield = 48.4 %; enantioselective reaction;
|
9 % ee |
|
With
hydrogen; benzylamine;
In
1,4-dioxane; water;
at 22.84 ℃;
under 750.075 Torr;
Reagent/catalyst;
|
71 % ee |
|
With
hydrogen; benzylamine;
In
1,4-dioxane; water;
at 22.84 ℃;
under 750.075 Torr;
Reagent/catalyst;
|
36 % ee |
|
With
palladium on activated charcoal; hydrogen; benzylamine; (1S,3R,4S,8S,9S)-9-hydroxy-cinchonane;
In
1,4-dioxane;
at 20 ℃;
enantioselective reaction;
Electrochemical reaction;
|
19 % ee |
|
With
palladium on activated charcoal; hydrogen; benzylamine; Cinchonidin;
In
1,4-dioxane;
at 20 ℃;
Reagent/catalyst;
enantioselective reaction;
Electrochemical reaction;
|
44 % ee |
|
With
C56H36F12FeO10P2Ru4; hydrogen;
In
ethanol; toluene;
at 100 ℃;
for 24h;
under 37503.8 Torr;
Reagent/catalyst;
enantioselective reaction;
Autoclave;
|
83 % ee |
|
With
C52H52FeO10P2Ru4; hydrogen;
In
ethanol; toluene;
at 100 ℃;
for 24h;
under 37503.8 Torr;
Reagent/catalyst;
enantioselective reaction;
Autoclave;
|
57 % ee |
|
With
5%-palladium/activated carbon; hydrogen; benzylamine; Cinchonidin;
In
1,4-dioxane; water;
at 22.84 ℃;
for 2h;
under 750.075 Torr;
Reagent/catalyst;
enantioselective reaction;
Kinetics;
|
83 % ee |
2,3-diphenylpropanoic acid
(E)-2,3-diphenylpropenoic acid
(S)-2,3-diphenylpropionic acid tert-butylammonium salt
2,3-diphenylacrylic acid
(S)-2,3-diphenyl-propionic acid methyl ester
(S)-2,3-diphenyl-1-propanol
(S)-2,3-Diphenyl-propionic acid ethyl ester
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