e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

Highly selective hydrolytic kinetic resolution of terminal epoxides catalyzed by chiral (salen) CoIII complexes. Practical synthesis of enantioenriched terminal epoxides …

…, BD Brandes, JF Larrow, M Tokunaga…

Index: Schaus, Scott E.; Brandes, Bridget D.; Larrow, Jay F.; Tokunaga, Makoto; Hansen, Karl B.; Gould, Alexandra E.; Furrow, Michael E.; Jacobsen, Eric N. Journal of the American Chemical Society, 2002 , vol. 124, # 7 p. 1307 - 1315

Full Text: HTML

Citation Number: 897

Abstract

The hydrolytic kinetic resolution (HKR) of terminal epoxides catalyzed by chiral (salen) CoIII complex 1⊙ OAc affords both recovered unreacted epoxide and 1, 2-diol product in highly enantioenriched form. As such, the HKR provides general access to useful, highly enantioenriched chiral building blocks that are otherwise difficult to access, from inexpensive racemic materials. The reaction has several appealing features from a ...

2-Vinyloxirane Structure

~38%

(R)-3-AMINOTETRAHYDROFURAN Structure

(R)-3-AMINOTETR...

(s)-2-vinyl-oxirane Structure

(s)-2-vinyl-oxirane

Learn More

2-Vinyloxirane Structure

~0%

(S)-3-Butene-1,2-diol Structure

(S)-3-Butene-1,...

(R)-3-AMINOTETRAHYDROFURAN Structure

(R)-3-AMINOTETR...

(s)-2-vinyl-oxirane Structure

(s)-2-vinyl-oxirane

Learn More

2-Vinyloxirane Structure

~39%

(R)-3-AMINOTETRAHYDROFURAN Structure

(R)-3-AMINOTETR...

2-Vinyloxirane Structure

(s)-2-vinyl-oxirane Structure

(s)-2-vinyl-oxirane

Learn More

Epifluorohydrin Structure

Epifluorohydrin

~0%

(2R)-3-fluoropropane-1,2-diol Structure

(2R)-3-fluoropr...

(S)-3-Fluoropropane-1,2-Diol Structure

(S)-3-Fluoropro...

(R)-3-fluoro-1,2-epoxypropane Structure

(R)-3-fluoro-1,...

Learn More

2-Vinyloxirane Structure

~0%

(R)-3-AMINOTETRAHYDROFURAN Structure

(R)-3-AMINOTETR...

(s)-2-vinyl-oxirane Structure

(s)-2-vinyl-oxirane

Learn More

2-Vinyloxirane Structure

~37%

(S)-3-Butene-1,2-diol Structure

(S)-3-Butene-1,...

(R)-3-AMINOTETRAHYDROFURAN Structure

(R)-3-AMINOTETR...

(s)-2-vinyl-oxirane Structure

(s)-2-vinyl-oxirane

Learn More

2-Vinyloxirane Structure

~0%

(R)-3-AMINOTETRAHYDROFURAN Structure

(R)-3-AMINOTETR...

2-Vinyloxirane Structure

(s)-2-vinyl-oxirane Structure

(s)-2-vinyl-oxirane

Learn More

epoxypropane Structure

~0%

(R)-(-)-1,2-Propanediol Structure

(R)-(-)-1,2-Pro...

(R)-(+)-Propylene oxide Structure

(R)-(+)-Propyle...

(S)-(−)-Propylene oxide Structure

(S)-(−)-Propyle...

Learn More

cobalt acetate tetrahydrate Structure

cobalt acetate ...

(1R,2R)-1,2-Bis[[[3,5-bis(tert-butyl)-2-hydroxyphenyl]methylene]amino]cyclohexane Structure

(1R,2R)-1,2-Bis...

~96%

(R,R)-(-)-N,N'-Bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminocobalt(II) Structure

(R,R)-(-)-N,N'-...

Learn More

epoxypropane Structure

~49%

(R)-(-)-1,2-Propanediol Structure

(R)-(-)-1,2-Pro...

(S)-(−)-Propylene oxide Structure

(S)-(−)-Propyle...

Learn More

epoxypropane Structure

~0%

(S)-(+)-1,2-Propanediol Structure

(S)-(+)-1,2-Pro...

(R)-(-)-1,2-Propanediol Structure

(R)-(-)-1,2-Pro...

(S)-(−)-Propylene oxide Structure

(S)-(−)-Propyle...

Learn More

epoxypropane Structure

~45%

(R)-(-)-1,2-Propanediol Structure

(R)-(-)-1,2-Pro...

(R)-(+)-Propylene oxide Structure

(R)-(+)-Propyle...

(S)-(−)-Propylene oxide Structure

(S)-(−)-Propyle...

Learn More

UNII:07FN14F351 Structure

UNII:07FN14F351

~0%

(R)-(-)-GLYCIDYL1-NAPHTHYLETHER Structure

(R)-(-)-GLYCIDY...

(S)-3-(naphthalen-1-yloxy)propane-1,2-diol Structure

(S)-3-(naphthal...

Learn More

UNII:07FN14F351 Structure

UNII:07FN14F351

~0%

S-(+)-α-Naphthyl Glycidyl Ether Structure

S-(+)-α-Naphthy...

(R)-(-)-GLYCIDYL1-NAPHTHYLETHER Structure

(R)-(-)-GLYCIDY...

(R)-3-(naphthalen-1-yloxy)propane-1,2-diol Structure

(R)-3-(naphthal...

Learn More

UNII:07FN14F351 Structure

UNII:07FN14F351

~0%

S-(+)-α-Naphthyl Glycidyl Ether Structure

S-(+)-α-Naphthy...

(R)-(-)-GLYCIDYL1-NAPHTHYLETHER Structure

(R)-(-)-GLYCIDY...

(S)-3-(naphthalen-1-yloxy)propane-1,2-diol Structure

(S)-3-(naphthal...

Learn More

phenyl glycidyl ether Structure

phenyl glycidyl...

~46%

phenyl glycidyl ether Structure

phenyl glycidyl...

(S)-1-phenyl glycerol Structure

(S)-1-phenyl gl...

Learn More

Epichlorohydrin Structure

Epichlorohydrin

~0%

(R)-(-)-Epichlorohydrin Structure

(R)-(-)-Epichlo...

(R)-3-Chloro-1,2-propanediol Structure

(R)-3-Chloro-1,...

(2S)-3-Chlorpropan-1,2-diol Structure

(2S)-3-Chlorpro...

Learn More

epoxypropane Structure

~0%

(S)-(+)-1,2-Propanediol Structure

(S)-(+)-1,2-Pro...

(R)-(-)-1,2-Propanediol Structure

(R)-(-)-1,2-Pro...

(S)-(−)-Propylene oxide Structure

(S)-(−)-Propyle...

Learn More

Styrene oxide Structure

~0%

(S)-Styrene oxide Structure

(S)-Styrene oxide

(R)-1-Phenyl-1,2-ethanediol Structure

(R)-1-Phenyl-1,...

styrene glycol Structure

Learn More

UNII:07FN14F351 Structure

UNII:07FN14F351

~0%

S-(+)-α-Naphthyl Glycidyl Ether Structure

S-(+)-α-Naphthy...

(R)-(-)-GLYCIDYL1-NAPHTHYLETHER Structure

(R)-(-)-GLYCIDY...

(R)-3-(naphthalen-1-yloxy)propane-1,2-diol Structure

(R)-3-(naphthal...

Learn More

UNII:07FN14F351 Structure

UNII:07FN14F351

~0%

S-(+)-α-Naphthyl Glycidyl Ether Structure

S-(+)-α-Naphthy...

(R)-(-)-GLYCIDYL1-NAPHTHYLETHER Structure

(R)-(-)-GLYCIDY...

(S)-3-(naphthalen-1-yloxy)propane-1,2-diol Structure

(S)-3-(naphthal...

Learn More

2-(3-Methoxyphenyl)oxirane Structure

2-(3-Methoxyphe...

~39%

(R)-3-Methoxystyreneoxide Structure

(R)-3-Methoxyst...

(1S)-1-(3-methoxyphenyl)ethane-1,2-diol Structure

(1S)-1-(3-metho...

Learn More

2-(4-chlorophenyl)oxirane Structure

2-(4-chlorophen...

~0%

2-(4-chlorophenyl)oxirane Structure

2-(4-chlorophen...

1-(4-chlorophenyl)ethane-1,2-diol Structure

1-(4-chlorophen...

(1R)-1-(4-Chlorophenyl)-1,2-ethanediol Structure

(1R)-1-(4-Chlor...

Learn More

2-(4-chlorophenyl)oxirane Structure

2-(4-chlorophen...

~0%

2-(4-chlorophenyl)oxirane Structure

2-(4-chlorophen...

(1R)-1-(4-Chlorophenyl)-1,2-ethanediol Structure

(1R)-1-(4-Chlor...

Learn More

Epichlorohydrin Structure

Epichlorohydrin

~43%

(R)-(-)-Epichlorohydrin Structure

(R)-(-)-Epichlo...

(R)-3-Chloro-1,2-propanediol Structure

(R)-3-Chloro-1,...

(2S)-3-Chlorpropan-1,2-diol Structure

(2S)-3-Chlorpro...

Learn More

1-Nitro-3-oxiranylbenzene Structure

1-Nitro-3-oxira...

~0%

(R)-(-)-(3-nitrophenyl)oxirane Structure

(R)-(-)-(3-nitr...

(2S)-2-(3-nitrophenyl)oxirane Structure

(2S)-2-(3-nitro...

(S)-(+)-1-(3-nitrophenyl)-1,2-ethanediol Structure

(S)-(+)-1-(3-ni...

Learn More

epoxypropane Structure

~47%

(S)-(+)-1,2-Propanediol Structure

(S)-(+)-1,2-Pro...

(R)-(-)-1,2-Propanediol Structure

(R)-(-)-1,2-Pro...

(S)-(−)-Propylene oxide Structure

(S)-(−)-Propyle...

Learn More

epoxypropane Structure

~0%

(R)-(-)-1,2-Propanediol Structure

(R)-(-)-1,2-Pro...

(R)-(+)-Propylene oxide Structure

(R)-(+)-Propyle...

(S)-(−)-Propylene oxide Structure

(S)-(−)-Propyle...

Learn More

Styrene oxide Structure

~0%

(S)-Styrene oxide Structure

(S)-Styrene oxide

(R)-1-Phenyl-1,2-ethanediol Structure

(R)-1-Phenyl-1,...

(S)-Styrene oxide Structure

(S)-Styrene oxide

Learn More

(+/-)-ethyl-3,4-epoxybutanoate Structure

(+/-)-ethyl-3,4...

~93%

ethyl (3r)-3,4-epoxybutyrate Structure

ethyl (3r)-3,4-...

(R)-ethyl 3,4-dihydroxybutanoate Structure

(R)-ethyl 3,4-d...

Learn More

(+/-)-ethyl-3,4-epoxybutanoate Structure

(+/-)-ethyl-3,4...

~44%

ethyl (3r)-3,4-epoxybutyrate Structure

ethyl (3r)-3,4-...

(R)-ethyl 3,4-dihydroxybutanoate Structure

(R)-ethyl 3,4-d...

(R)-ethyl 3,4-dihydroxybutanoate Structure

(R)-ethyl 3,4-d...

Learn More

Epibromohydrin Structure

~91%

(R)-3-BROMOPROPANE-1,2-DIOL Structure

(R)-3-BROMOPROP...

Oxirane, 2-(bromomethyl)-, (2S) Structure

Oxirane, 2-(bro...

Learn More

Epibromohydrin Structure

~92%

(R)-3-BROMOPROPANE-1,2-DIOL Structure

(R)-3-BROMOPROP...

(R)-Epibromohydrine Structure

(R)-Epibromohydrine

Oxirane, 2-(bromomethyl)-, (2S) Structure

Oxirane, 2-(bro...

Learn More

(+/-)-ethyl-3,4-epoxybutanoate Structure

(+/-)-ethyl-3,4...

~42%

ethyl (s)-3,4-epoxybutanoate Structure

ethyl (s)-3,4-e...

(R)-ethyl 3,4-dihydroxybutanoate Structure

(R)-ethyl 3,4-d...

(R)-ethyl 3,4-dihydroxybutanoate Structure

(R)-ethyl 3,4-d...

Learn More

(+/-)-ethyl-3,4-epoxybutanoate Structure

(+/-)-ethyl-3,4...

~44%

ethyl (s)-3,4-epoxybutanoate Structure

ethyl (s)-3,4-e...

(R)-ethyl 3,4-dihydroxybutanoate Structure

(R)-ethyl 3,4-d...

Learn More

Styrene oxide Structure

~44%

(S)-Styrene oxide Structure

(S)-Styrene oxide

(R)-1-Phenyl-1,2-ethanediol Structure

(R)-1-Phenyl-1,...

styrene glycol Structure

Learn More

Styrene oxide Structure

~0%

(S)-Styrene oxide Structure

(S)-Styrene oxide

(R)-1-Phenyl-1,2-ethanediol Structure

(R)-1-Phenyl-1,...

(S)-Styrene oxide Structure

(S)-Styrene oxide

Learn More

Epichlorohydrin Structure

Epichlorohydrin

~0%

(R)-(-)-Epichlorohydrin Structure

(R)-(-)-Epichlo...

(R)-3-Chloro-1,2-propanediol Structure

(R)-3-Chloro-1,...

(2S)-3-Chlorpropan-1,2-diol Structure

(2S)-3-Chlorpro...

Learn More

2-(Trifluoromethyl)oxirane Structure

2-(Trifluoromet...

~0%

1,1,1-TRIFLUORO-2,3-EPOXYPROPANE Structure

1,1,1-TRIFLUORO...

(S)-(-)-1,2-Dihydroxy-3,3,3-trifluoropropane Structure

(S)-(-)-1,2-Dih...

2-(Trifluoromethyl)oxirane Structure

2-(Trifluoromet...

Learn More

Epibromohydrin Structure

~90%

(S)-3-Bromopropane-1,2-diol Structure

(S)-3-Bromoprop...

(R)-Epibromohydrine Structure

(R)-Epibromohydrine

Learn More

Epibromohydrin Structure

~92%

(S)-3-Bromopropane-1,2-diol Structure

(S)-3-Bromoprop...

(R)-Epibromohydrine Structure

(R)-Epibromohydrine

Oxirane, 2-(bromomethyl)-, (2S) Structure

Oxirane, 2-(bro...

Learn More

2-(3-chlorophenyl)oxirane Structure

2-(3-chlorophen...

~0%

2-(3-chlorophenyl)oxirane Structure

2-(3-chlorophen...

1,2-Ethanediol, 1-(3-chlorophenyl)-, (1S) Structure

1,2-Ethanediol,...

(1R)-1-(3-Chlorophenyl)-1,2-ethanediol Structure

(1R)-1-(3-Chlor...

Learn More

2-(3-chlorophenyl)oxirane Structure

2-(3-chlorophen...

~0%

(2S)-2-(3-chlorophenyl)oxirane Structure

(2S)-2-(3-chlor...

1,2-Ethanediol, 1-(3-chlorophenyl)-, (1S) Structure

1,2-Ethanediol,...

(1R)-1-(3-Chlorophenyl)-1,2-ethanediol Structure

(1R)-1-(3-Chlor...

Learn More

N/A Structure

~36%

Carbamic acid, [(2S)-2,3-dihydroxypropyl]-, 1,1-dimethylethyl ester (9CI) Structure

Carbamic acid, ...

Carbamic acid, [(2R)-2,3-dihydroxypropyl]-, 1,1-dimethylethyl ester (9CI) Structure

Carbamic acid, ...

(S)-1-(4-CHLOROPHENYL)-2,2,2-TRIFLUOROETHYLAMINEHCL Structure

(S)-1-(4-CHLORO...

Learn More

N/A Structure

~37%

Carbamic acid, [(2R)-2,3-dihydroxypropyl]-, 1,1-dimethylethyl ester (9CI) Structure

Carbamic acid, ...

(S)-1-(4-CHLOROPHENYL)-2,2,2-TRIFLUOROETHYLAMINEHCL Structure

(S)-1-(4-CHLORO...

Learn More

Styrene oxide Structure

~0%

(S)-Styrene oxide Structure

(S)-Styrene oxide

(R)-1-Phenyl-1,2-ethanediol Structure

(R)-1-Phenyl-1,...

styrene glycol Structure

Learn More

Styrene oxide Structure

~43%

(S)-Styrene oxide Structure

(S)-Styrene oxide

(R)-1-Phenyl-1,2-ethanediol Structure

(R)-1-Phenyl-1,...

(S)-Styrene oxide Structure

(S)-Styrene oxide

Learn More

Glycidyl butyrate Structure

Glycidyl butyrate

~45%

(R)-Glycidyl butyrate Structure

(R)-Glycidyl bu...

N/A Structure

Learn More

Glycidic Acid Methyl Ester Structure

Glycidic Acid M...

~0%

Methyl glycerate Structure

Methyl glycerate

methyl (S)-glycerate Structure

methyl (S)-glycerate

Glycidic Acid Methyl Ester Structure

Glycidic Acid M...

Learn More

Glycidic Acid Methyl Ester Structure

Glycidic Acid M...

~0%

methyl (S)-glycerate Structure

methyl (S)-glycerate

Glycidic Acid Methyl Ester Structure

Glycidic Acid M...

Learn More

2-Vinyloxirane Structure

~38%

(S)-3-Butene-1,2-diol Structure

(S)-3-Butene-1,...

2-Vinyloxirane Structure

Learn More

2-Vinyloxirane Structure

~0%

(S)-3-Butene-1,2-diol Structure

(S)-3-Butene-1,...

(R)-3-AMINOTETRAHYDROFURAN Structure

(R)-3-AMINOTETR...

(s)-2-vinyl-oxirane Structure

(s)-2-vinyl-oxirane

Learn More

2-((Benzyloxy)methyl)oxirane Structure

2-((Benzyloxy)m...

~48%

(S)-(-)-3-Benzyloxy-1,2-propanediol Structure

(S)-(-)-3-Benzy...

(R)-(-)-Benzyl glycidyl ether Structure

(R)-(-)-Benzyl ...

Learn More

2-((Benzyloxy)methyl)oxirane Structure

2-((Benzyloxy)m...

~48%

(R)-(+)-3-Benzyloxy-1,2-propanediol Structure

(R)-(+)-3-Benzy...

(S)-(-)-3-Benzyloxy-1,2-propanediol Structure

(S)-(-)-3-Benzy...

(R)-(-)-Benzyl glycidyl ether Structure

(R)-(-)-Benzyl ...

Learn More

Glycidic Acid Methyl Ester Structure

Glycidic Acid M...

~37%

methyl (S)-glycerate Structure

methyl (S)-glycerate

Glycidic Acid Methyl Ester Structure

Glycidic Acid M...

Glycidic Acid Methyl Ester Structure

Glycidic Acid M...

Learn More

2-(Trifluoromethyl)oxirane Structure

2-(Trifluoromet...

~40%

(S)-(-)-1,2-Dihydroxy-3,3,3-trifluoropropane Structure

(S)-(-)-1,2-Dih...

2-(Trifluoromethyl)oxirane Structure

2-(Trifluoromet...

Learn More

2-(Trifluoromethyl)oxirane Structure

2-(Trifluoromet...

~0%

1,1,1-TRIFLUORO-2,3-EPOXYPROPANE Structure

1,1,1-TRIFLUORO...

(S)-(-)-1,2-Dihydroxy-3,3,3-trifluoropropane Structure

(S)-(-)-1,2-Dih...

2-(Trifluoromethyl)oxirane Structure

2-(Trifluoromet...

Learn More

Preparation of enantioenriched tetraols and triolamines from...

[Kaviani-Joupari, Makan; Schramm, Michael P. Tetrahedron Letters, 2013 , vol. 54, # 37 p. 5014 - 5017]

“Cassette” In Situ Enzymatic Screening Identifies Complement...

[Dey, Sangeeta; Powell, Douglas R.; Hu, Chunhua; Berkowitz, David B. Angewandte Chemie - International Edition, 2007 , vol. 46, # 37 p. 7010 - 7014]

Preparation of enantioenriched tetraols and triolamines from...

[Kaviani-Joupari, Makan; Schramm, Michael P. Tetrahedron Letters, 2013 , vol. 54, # 37 p. 5014 - 5017]

Synthesis and stereospecificity of 4, 5-disubstituted oxazol...

[Orac, Crina M.; Zhou, Shu; Means, John A.; Boehm, David; Bergmeier, Stephen C.; Hines, Jennifer V. Journal of Medicinal Chemistry, 2011 , vol. 54, # 19 p. 6786 - 6795]

Kinetic chiral resolutions of 1, 2-diols and desymmetrizatio...

[Keith Chenault; Chafin, Laura F.; Liehr, Sebastian Journal of Organic Chemistry, 1998 , vol. 63, # 12 p. 4039 - 4045]