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inquirydiazomethane
ethyl cinnamate
ethyl rac-(1S,2S)-2-phenylcycloproanecarboxylate
Conditions | Yield |
---|---|
With palladium diacetate In diethyl ether for 1h; Ambient temperature; | 98% |
styrene
diazoacetic acid ethyl ester
ethyl rac-(1S,2S)-2-phenylcycloproanecarboxylate
Conditions | Yield |
---|---|
With [Ru(4-F-TPP)(BIMe)2] In dichloromethane at 20℃; for 0.333333h; Inert atmosphere; | 98% |
With dirhodium tetraacetate In dichloromethane for 24h; Inert atmosphere; | 89% |
With hemin; glycine ethyl ester hydrochloride; acetic acid; sodium nitrite In water at 40℃; for 24h; | 50% |
With sodium dithionite; κ-NHis-(apo heme myoglobin H64V mutant)-κ-C-(2-ethoxy-2-oxoethylidene)ruthenium mesoporphyrin IX In aq. phosphate buffer at 20℃; for 18h; pH=7; Catalytic behavior; Reagent/catalyst; pH-value; Inert atmosphere; Sealed tube; Green chemistry; Enzymatic reaction; diastereoselective reaction; | 8.4 %Chromat. |
ethanol
trans-2-phenylcyclopropane-1-carboxylic acid
ethyl rac-(1S,2S)-2-phenylcycloproanecarboxylate
Conditions | Yield |
---|---|
With hydrogenchloride for 8h; Heating; | 92% |
With toluene-4-sulfonic acid Reflux; | 91% |
styrene oxide
diethoxyphosphoryl-acetic acid ethyl ester
ethyl rac-(1S,2S)-2-phenylcycloproanecarboxylate
Conditions | Yield |
---|---|
Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With n-butyllithium In 1,4-dioxane at 0℃; for 0.5h; Stage #2: styrene oxide at 135℃; for 1h; Microwave irradiation; | 91% |
With n-butyllithium In 1,2-dimethoxyethane at 135℃; for 1h; Microwave irradiation; |
ethanol
(1S*,2R*)-2-phenylcyclopropane-1-carboxylic acid
ethyl rac-(1S,2S)-2-phenylcycloproanecarboxylate
Conditions | Yield |
---|---|
With hydrogenchloride for 8h; Heating; | 89% |
diazomethane
diazoacetic acid ethyl ester
benzaldehyde
ethyl rac-(1S,2S)-2-phenylcycloproanecarboxylate
Conditions | Yield |
---|---|
Stage #1: diazoacetic acid ethyl ester; benzaldehyde With copper(l) iodide; triphenylphosphine In dichloromethane at 40℃; Inert atmosphere; Stage #2: diazomethane With tris(dibenzylideneacetone)dipalladium (0) In dichloromethane at -78℃; Inert atmosphere; diastereoselective reaction; | 85% |
Conditions | Yield |
---|---|
With palladium diacetate; caesium carbonate; catacxium A In water; toluene at 110℃; for 12h; Suzuki-Miyaura Coupling; Inert atmosphere; Reflux; diastereoselective reaction; | 84% |
trimethylsulfoxonium iodide
ethyl cinnamate
ethyl rac-(1S,2S)-2-phenylcycloproanecarboxylate
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran; dimethyl sulfoxide at 25℃; Inert atmosphere; | 79% |
Stage #1: trimethylsulfoxonium iodide With sodium hydride In dimethyl sulfoxide for 1h; Inert atmosphere; Stage #2: ethyl cinnamate In dimethyl sulfoxide at 0 - 65℃; for 108h; Inert atmosphere; | |
Stage #1: trimethylsulfoxonium iodide With sodium hydride In dimethyl sulfoxide for 1h; Inert atmosphere; Stage #2: ethyl cinnamate In dimethyl sulfoxide at 0 - 65℃; for 108h; Inert atmosphere; |
Conditions | Yield |
---|---|
With (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile In dimethyl sulfoxide at 35℃; for 3h; Inert atmosphere; Sealed tube; Irradiation; chemoselective reaction; | 75% |
Conditions | Yield |
---|---|
Stage #1: (E)-ethyl 2-(benzenesulfinyl)cyclopropane-1-carboxylate With isopropylmagnesium chloride In tetrahydrofuran at -78℃; for 0.166667h; Inert atmosphere; Stage #2: With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; zinc(II) chloride In tetrahydrofuran at 0℃; for 1h; Negishi Coupling; Inert atmosphere; Stage #3: bromobenzene In tetrahydrofuran at 25℃; for 15h; Negishi Coupling; Inert atmosphere; | 74% |
styrene
diazoacetic acid ethyl ester
ethyl rac-(1S,2S)-2-phenylcycloproanecarboxylate
cis-1-ethoxycarbonyl-2-phenylcyclopropane
C
diethyl Fumarate
Conditions | Yield |
---|---|
With dirhodium tetraacetate In dichloromethane at 20℃; for 1.58333h; Reagent/catalyst; | A 72% B n/a C 7 %Spectr. |
Conditions | Yield |
---|---|
With [4,4’-bis(1,1-dimethylethyl)-2,2’-bipyridine-N1,N1‘]bis [3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C]iridium(III) hexafluorophosphate In dimethyl sulfoxide at 20℃; for 24h; Inert atmosphere; Irradiation; | 72% |
styrene
glycine ethyl ester hydrochloride
ethyl rac-(1S,2S)-2-phenylcycloproanecarboxylate
cis-1-ethoxycarbonyl-2-phenylcyclopropane
Conditions | Yield |
---|---|
With meso-tetraphenylporphyrin iron(III) chloride; acetic acid; sodium nitrite In water at 40℃; for 14h; optical yield given as %de; diastereoselective reaction; | A 71% B n/a |
With sulfuric acid; sodium nitrite; iodo(5,10,15,20-tetraphenylporphyrinato-κ4N)rhodium(III) In dichloromethane; water at 20℃; for 96h; | A 31% B 31% |
With meso-tetraphenylporphyrin iron(III) chloride; acetic acid; sodium nitrite In water at 40℃; for 15h; Overall yield = 73 %; Overall yield = 133 mg; diastereoselective reaction; | A n/a B n/a |
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran for 7h; Heating; | 70% |
styrene
diazoacetic acid ethyl ester
ethyl rac-(1S,2S)-2-phenylcycloproanecarboxylate
cis-1-ethoxycarbonyl-2-phenylcyclopropane
Conditions | Yield |
---|---|
With copper acetylacetonate; phenylhydrazine In dichloromethane at 40℃; optical yield given as %de; | A 67% B 27% |
With sodium tetrachloroaurate dihydrate; 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate at 20℃; for 26h; optical yield given as %de; chemoselective reaction; | A 62% B 32% |
With chiral 2,2'-bipyridyl ligand; copper(II) bis(trifluoromethanesulfonate); phenylhydrazine In dichloromethane at 20℃; for 12h; | A 58% B n/a |
(2-oxo-5-phenyltetrahydrofuran-3-yl)-phosphonic acid diethyl ester
ethanol
ethyl rac-(1S,2S)-2-phenylcycloproanecarboxylate
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran for 8h; Heating; | 65% |
styrene
diazoacetic acid ethyl ester
ethyl rac-(1S,2S)-2-phenylcycloproanecarboxylate
cis-1-ethoxycarbonyl-2-phenylcyclopropane
C
Diethyl maleate
Conditions | Yield |
---|---|
With [Fe(tpfc)Cl] at 22 - 25℃; Product distribution; Further Variations:; Reagents; | A 53% B 36% C 9% |
5,10,15,20-tetraphenylporphyrinato ruthenium carbonyl for 1h; Product distribution; Ambient temperature; various catalysts; also a chiral porphyrin as catalyst; | |
5,10,15,20-tetraphenylporphyrinato ruthenium carbonyl for 1h; Ambient temperature; Title compound not separated from byproducts; | |
With Co(N-Me-NCTPP)py In toluene at 20℃; Inert atmosphere; optical yield given as %de; diastereoselective reaction; | A n/a B n/a C 15 %Chromat. |
ethyl 2-phenylcyclopropylcarboxylate
ethyl rac-(1S,2S)-2-phenylcycloproanecarboxylate
cis-1-ethoxycarbonyl-2-phenylcyclopropane
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol; water for 5h; Reflux; optical yield given as %de; | A n/a B 50% |
styrene
diazoacetic acid ethyl ester
methanol
A
2-methoxyethyl acetate
ethyl rac-(1S,2S)-2-phenylcycloproanecarboxylate
cis-1-ethoxycarbonyl-2-phenylcyclopropane
D
diethyl Fumarate
E
Diethyl maleate
Conditions | Yield |
---|---|
With (tetra-n-butylammonium)4-[γ-H2SiW10O36Cu(II)2(μ-1,1-N3)2] at 59.84℃; under 760.051 Torr; Inert atmosphere; optical yield given as %de; chemoselective reaction; | A 42% B n/a C n/a D n/a E n/a |
trans-2-phenylcyclopropane-1-carboxylic acid
Triethyl orthoacetate
ethyl rac-(1S,2S)-2-phenylcycloproanecarboxylate
Conditions | Yield |
---|---|
With rhizopus oryzae lipase In toluene at 50℃; for 48h; Catalytic behavior; Reagent/catalyst; Enzymatic reaction; | 41% |
styrene
diazoacetic acid ethyl ester
ethyl rac-(1S,2S)-2-phenylcycloproanecarboxylate
cis-1-ethoxycarbonyl-2-phenylcyclopropane
C
but-2-enedioic acid diethyl ester
Conditions | Yield |
---|---|
With μ-oxo-diiron octapropylporphyrazine In toluene at 70℃; for 8h; Inert atmosphere; | A n/a B n/a C 38% |
With μ-oxo-diiron octapropylporphyrazine In toluene at 70℃; for 1h; Catalytic behavior; Reagent/catalyst; Temperature; Inert atmosphere; | A n/a B n/a C 8% |
With [Cu(1,3,5-tris(thiocyanatomethyl)mesitylene)]2[B(C6H3(CF3)2)4]2 In dichloromethane for 7h; optical yield given as %de; |
ethyl rac-(1S,2S)-2-phenylcycloproanecarboxylate
cis-1-ethoxycarbonyl-2-phenylcyclopropane
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride In tetrahydrofuran at -78 - 20℃; | A 31% B 18% |
styrene oxide
ethyl (triphenylphosphoranylidene)acetate
ethyl rac-(1S,2S)-2-phenylcycloproanecarboxylate
Conditions | Yield |
---|---|
at 190 - 200℃; |
cis-1-ethoxycarbonyl-2-phenylcyclopropane
ethyl rac-(1S,2S)-2-phenylcycloproanecarboxylate
Conditions | Yield |
---|---|
With lithium diisopropyl amide Product distribution; cis-trans isomerization in several aprotic solvents with several reaction times; |
styrene
diazoacetic acid ethyl ester
ethyl rac-(1S,2S)-2-phenylcycloproanecarboxylate
cis-1-ethoxycarbonyl-2-phenylcyclopropane
C
diethyl Fumarate
D
Diethyl maleate
Conditions | Yield |
---|---|
With 2,9-bis(2,6-bis(1,4,7-trioxaoctyl)phenyl)-1,10-phenanthroline; copper(I) triflate In dichloromethane; 1,2-dichloro-ethane at 20℃; for 24h; Product distribution; var. of reagent, temp.; | A 82 % Chromat. B 18 % Chromat. C 93 % Chromat. D 7 % Chromat. |
tetrahydridotris(triphenylphosphine)osmium(IV) at 100℃; for 4h; Product distribution; Mechanism; other olefins, other temperature and reaction time; competition with cyclooctene, other catalyst: Rh2(OAc)4; | |
1,4,7,10,17,20,23,26-octaoxa-16,32-(1,10-phenantholin-2,9-diyl)-<10.10>metacyclophane; copper(I) triflate In dichloromethane; 1,2-dichloro-ethane at 20℃; for 24h; Yield given. Yields of byproduct given; |
styrene
diphenylsulfonium 2-ethoxy-2-oxoethylide
ethyl rac-(1S,2S)-2-phenylcycloproanecarboxylate
cis-1-ethoxycarbonyl-2-phenylcyclopropane
Conditions | Yield |
---|---|
With diazoacetic acid ethyl ester; dirhodium tetraacetate In 1,2-dichloro-ethane for 20h; Product distribution; Heating; in the presence of Ph2S as well; |
ethyl rac-(1S,2S)-2-phenylcycloproanecarboxylate
Conditions | Yield |
---|---|
With potassium tert-butylate | |
With ammonia; sodium amide | |
With sodium methylate |
diazomethane
ethyl cinnamate
ethyl rac-(1S,2S)-2-phenylcycloproanecarboxylate
cis-1-ethoxycarbonyl-2-phenylcyclopropane
Conditions | Yield |
---|---|
With palladium (II) ion |
styrene
diazoacetic acid ethyl ester
A
ethyl (1S,2R)-2-phenylcyclopropylcarboxylate
B
(1R,2S)-ethyl 2-phenylcyclopropane-1-carboxylate
ethyl rac-(1S,2S)-2-phenylcycloproanecarboxylate
Conditions | Yield |
---|---|
With thallium(I) hexafluorophosphate; RuCl[(S)-N,N'-(bis(o-(Ph2P)PhCH)-6,6'-diMe-1,1'-biPh2-diNH2] In dichloromethane for 14h; | |
With copper(I) trifluoromethanesulfonate benzene; chiral bisoxazoline containing 2,5-diaryl-1,3,4-oxadiazole In 1,2-dichloro-ethane at 20℃; for 24h; Product distribution; Further Variations:; Reagents; Temperatures; | |
chiral α-amino acid-based borate copper catalyst In benzene at 0℃; Title compound not separated from byproducts; | |
With sodium dithionite; P450 CYP119 In ethanol at 24℃; for 1h; Enzymatic reaction; Overall yield = 20 %Chromat.; Optical yield = 25 %ee; enantioselective reaction; |
ethyl rac-(1S,2S)-2-phenylcycloproanecarboxylate
trans-(3-phenylcyclopropyl)methanol
Conditions | Yield |
---|---|
With diisobutylaluminium hydride In diethyl ether; toluene at -78℃; for 0.5h; Inert atmosphere; | 96% |
With lithium aluminium tetrahydride In diethyl ether Heating; | |
With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 1.5h; | 1.04 g |
ethyl rac-(1S,2S)-2-phenylcycloproanecarboxylate
trans-2-phenylcyclopropane-1-carboxylic acid
Conditions | Yield |
---|---|
With ethanol; potassium hydroxide at 20℃; | 93% |
With Rhizopus sp. protease; water In aq. phosphate buffer; acetone at 20℃; for 3.5h; pH=7.0; Catalytic behavior; Reagent/catalyst; Time; Enzymatic reaction; | 92% |
With water; lithium hydroxide In ethanol for 1h; Reflux; | 90% |
ethyl rac-(1S,2S)-2-phenylcycloproanecarboxylate
hexan-1-ol
A
dihexyl ether
Conditions | Yield |
---|---|
With sulfuric acid at 130℃; for 12h; | A n/a B 93% |
ethyl rac-(1S,2S)-2-phenylcycloproanecarboxylate
trans-2-phenylcyclopropanecarbaldehyde
Conditions | Yield |
---|---|
With diisobutylaluminium hydride In hexane at -75℃; for 1h; | 85% |
Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 1.5 h / 20 °C 2: sulfur trioxide pyridine complex; triethylamine / dimethyl sulfoxide; dichloromethane / 1.5 h / 0 - 20 °C View Scheme | |
Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride / diethyl ether / 6 h / Inert atmosphere; Reflux 2: pyridinium chlorochromate / dichloromethane / 3 h / 20 °C / Inert atmosphere View Scheme |
ethyl rac-(1S,2S)-2-phenylcycloproanecarboxylate
A
ethyl (S,S)-2-phenylcyclopropane-1-carboxylate
B
(1R,2R)-2-phenyl-cyclopropanecarboxylic acid ethyl ester
trans-2-phenylcyclopropane-1-carboxylic acid
Conditions | Yield |
---|---|
With novozyme 435; water In aq. phosphate buffer; acetone at 20℃; for 24h; pH=7.0; Catalytic behavior; Reagent/catalyst; Time; Resolution of racemate; Enzymatic reaction; enantioselective reaction; | A n/a B n/a C 78% |
ethyl rac-(1S,2S)-2-phenylcycloproanecarboxylate
ethyl 4-phenylbutyrate
Conditions | Yield |
---|---|
With N,N,N,N,N,N-hexamethylphosphoric triamide; samarium diiodide; tert-butyl alcohol In tetrahydrofuran at 0℃; for 1h; | 74% |
With N,N,N,N,N,N-hexamethylphosphoric triamide; samarium diiodide In tetrahydrofuran; tert-butyl alcohol for 1h; | 73% |
With N,N,N,N,N,N-hexamethylphosphoric triamide; samarium diiodide; tert-butyl alcohol In tetrahydrofuran for 12h; Product distribution; Mechanism; Ambient temperature; var. temperature, var. time, other 2- and 2,3-disubstituted cyclopropanecarboxylates; | 11% |
ethyl rac-(1S,2S)-2-phenylcycloproanecarboxylate
Conditions | Yield |
---|---|
With chlorosulfonic acid In dichloromethane at 0 - 20℃; for 3h; | 64% |
ethyl rac-(1S,2S)-2-phenylcycloproanecarboxylate
Conditions | Yield |
---|---|
With N,N,N,N,N,N-hexamethylphosphoric triamide; samarium diiodide; tert-butyl alcohol-d In tetrahydrofuran for 1h; | 63% |
ethyl rac-(1S,2S)-2-phenylcycloproanecarboxylate
A
ethyl (S,S)-2-phenylcyclopropane-1-carboxylate
B
(1R,2R)-trans-2-phenyl-1-cyclopropanecarboxylic acid
Conditions | Yield |
---|---|
With novozyme 435; sodium hydroxide In water; acetone at 20℃; pH=7.4; Resolution of racemate; Enzymatic reaction; enantioselective reaction; | A n/a B 45% |
Conditions | Yield |
---|---|
Stage #1: acetonitrile With sodium hydride In 1,4-dioxane; mineral oil for 0.5h; Stage #2: ethyl rac-(1S,2S)-2-phenylcycloproanecarboxylate In 1,4-dioxane; mineral oil at 100℃; for 3h; | 40% |
With hydrogenchloride; sodium hydride In 1,4-dioxane; mineral oil at 100℃; for 3h; | 40% |
Stage #1: acetonitrile With sodium hydride In 1,4-dioxane; mineral oil for 0.5h; Stage #2: ethyl rac-(1S,2S)-2-phenylcycloproanecarboxylate In 1,4-dioxane; mineral oil at 100℃; for 3h; | 40% |
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