The Experts below are selected from a list of 288 Experts worldwide ranked by ideXlab platform
Stephen F. Martin - One of the best experts on this subject based on the ideXlab platform.
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Organic Syntheses - (2S)‐(−)‐3‐exo‐(Dimethylamino)Isoborneol [(2S)‐(−)‐DAIB]
Organic Syntheses, 2003Co-Authors: James D. White, Duncan J. Wardrop, Kurt F. Sundermann, Christopher E. Neipp, Stephen F. MartinAbstract:(2S)-(−)-3-exo-(Dimethylamino)Isoborneol, [(2S)-(−)-DAIB] R (−)-Camphorquinone 1 I (2S)-(−)-3-exo-AminoIsoborneol 2 (1R,2S,6R,7S)-1,10,10-Trimethyl-4-oxo-5-aza-3-oxatricyclo [5.2.1.0] decone 3 N-methyl-(1R,2S,6R,7S)-1,10,10-trimethyl-4-oxo-5-aza-3-oxatricyclo [5.2.1.0] decone 4 P (2S)-(−)-3-(−)-exo-(Dimethylamino)Isoborneol 5 Keywords: amines (and salts), aliphatic; alcohols and diols, substituted; reduction, CN CH2NH2; annulation, heterocyclic-[5]; heterocycles, five-membered, one nitrogen, one oxygen; alkylation, N-alkylation; acylation (including formylation and Friedel-Crafts reactions); alkylation, N-alkylation; heterocycles, five-membered, one nitrogen, one oxygen; reduction, miscellaneous; amines (and salts), aliphatic; alcohols and diols, substituted; DAIB, decomposition in air
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2s 3 exo dimethylamino Isoborneol 2s daib
Organic Syntheses, 2003Co-Authors: James D. White, Duncan J. Wardrop, Kurt F. Sundermann, Christopher E. Neipp, Stephen F. MartinAbstract:(2S)-(−)-3-exo-(Dimethylamino)Isoborneol, [(2S)-(−)-DAIB] R (−)-Camphorquinone 1 I (2S)-(−)-3-exo-AminoIsoborneol 2 (1R,2S,6R,7S)-1,10,10-Trimethyl-4-oxo-5-aza-3-oxatricyclo [5.2.1.0] decone 3 N-methyl-(1R,2S,6R,7S)-1,10,10-trimethyl-4-oxo-5-aza-3-oxatricyclo [5.2.1.0] decone 4 P (2S)-(−)-3-(−)-exo-(Dimethylamino)Isoborneol 5 Keywords: amines (and salts), aliphatic; alcohols and diols, substituted; reduction, CN CH2NH2; annulation, heterocyclic-[5]; heterocycles, five-membered, one nitrogen, one oxygen; alkylation, N-alkylation; acylation (including formylation and Friedel-Crafts reactions); alkylation, N-alkylation; heterocycles, five-membered, one nitrogen, one oxygen; reduction, miscellaneous; amines (and salts), aliphatic; alcohols and diols, substituted; DAIB, decomposition in air
William A Nugent - One of the best experts on this subject based on the ideXlab platform.
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Organic Syntheses - (2S)‐(−)‐3‐exo‐(Morpholino)Isoborneol [(−)‐MIB]
Organic Syntheses, 2005Co-Authors: Young K. Chen, Sang-jin Jeon, Patrick J Walsh, William A NugentAbstract:Anti-(1-R)-(1)-Camphorquinone 3-oxime (1R)-(+)-Camphor (2S)-(−)-3-exo-AminoIsoborneol Bis(2-bromoethyl) ether Lithium aluminum hydride Isoamyl nitrite Potassium-tert-butoxide Triethylamine Keywords: camphorquinone oxime; (morpholino)Isoborneol; chiral ligand; substituted aldehydes; additions; enantiomers
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2s 3 exo morpholino Isoborneol mib
Organic Syntheses, 2005Co-Authors: Young K. Chen, Sang-jin Jeon, Patrick J Walsh, William A NugentAbstract:Anti-(1-R)-(1)-Camphorquinone 3-oxime (1R)-(+)-Camphor (2S)-(−)-3-exo-AminoIsoborneol Bis(2-bromoethyl) ether Lithium aluminum hydride Isoamyl nitrite Potassium-tert-butoxide Triethylamine Keywords: camphorquinone oxime; (morpholino)Isoborneol; chiral ligand; substituted aldehydes; additions; enantiomers
Maria C. Aversa - One of the best experts on this subject based on the ideXlab platform.
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Synthesis of Enantiomerically Pure Bis‐Sulfinyl Substituted Phenylene Ethynylenes
Helvetica Chimica Acta, 2014Co-Authors: Anna Barattucci, Maria C. Aversa, Elisa Deni, Teresa Papalia, Paola BonaccorsiAbstract:The stereoselective and efficient monoaddition of transient [(1S,2R,4R)-2-hydroxy-7,7-dimethylbicyclo[2.2.1]hept-1-yl]methanesulfenic (=(1S)-Isoborneol-10-sulfenic) acid to isomeric diethynylbenzenes affords {1-[(1S)-Isoborneol-10-sulfinyl]ethenyl}ethynylbenzenes. Their enantiomerically pure (RS)-epimers are involved in a Cu-free Sonogashira coupling with 1,4-diiodo-2,5-dimethoxybenzene to give C2-symmetric bis-sulfinyl phenylene ethynylenes, stimulating prototypes of new sulfurated chiral architectures that can find application as chelating agents.
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diels alder reactions of enantiopure 1s Isoborneol 10 sulfinyl and 1s exo 2 bornylsulfinyl vinylcyclohexenes with maleimides
Tetrahedron-asymmetry, 1999Co-Authors: Maria C. Aversa, Anna Barattucci, Paola Bonaccorsi, Placido Giannetto, Francesco Nicolò, Simona RizzoAbstract:Abstract Uncatalyzed cycloadditions of enantiopure [(1 S )-Isoborneol-10-sulfinyl]- and [(1 S - exo )-2-bornylsulfinyl]vinylcyclohexenes with N -phenylmaleimide occur with good facial diastereoselectivity, controlled by the sulfur configuration, even if the extent of this stereoselection appears influenced by the structural features of the terpene residue directly linked to the sulfoxide moiety. Complete endo diastereoselectivity is observed in LiClO 4 catalyzed cycloadditions of ( R S )-1-{1-[(1 S )-Isoborneol-10-sulfinyl]- and ( S S )-1-{1-[(1 S-exo )-2-bornylsulfinyl]vinyl}cyclohexenes 4 and 5 , respectively. The Diels–Alder reactivity of 5 and ( S S , E )-1-{2-[(1 S-exo )-2-bornylsulfinyl]vinyl}cyclohexene 7 , with the chiral auxiliary being in a different position with respect to the diene moiety, is also compared, and the results obtained comfirm that 1-sulfinyldienes are less reactive than 2-sulfinyldienes. SnCl 4 catalyzed cycloaddition of 7 with N -methylmaleimide is also performed.
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Enantiopure sulfinylthiopyrans and related compounds from alkylsulfinylbuta-1,3-dienes
Tetrahedron: Asymmetry, 1999Co-Authors: Maria C. Aversa, Anna Barattucci, Paola Bonaccorsi, Placido Giannetto, Bianca F. Bonini, Francesco NicolòAbstract:Uncatalyzed and LiClO4 catalyzed cycloadditions of (RS)-1-{1-[(1S)-Isoborneol-10-sulfinyl]vinyl}cyclohexene 1 and (RS,E)-3-[(1S)-Isoborneol-10-sulfinyl]-1-methoxybuta-1,3-diene 2 with di(p-tolyl)- and di(p-anisyl)thioketones 3 and 4 occur with complete regioselectivity. The lack of facial diastereoselectivity, observed in the cycloadditions of 1 with 3 or 4, appears to be a consequence of the sterical features of both diene and dienophile which, in the transition states, make the topological differentiation induced by the presence of the alkylsulfinyl group as chiral auxiliary uninfluential. No significant improvement in diastereoselectivity is observed in the LiClO4 catalyzed reactions, but the obtained enantiopure cycloadducts are easily separated by column chromatography and isolated in high yields. © 1999 Elsevier Science Ltd. All rights reserved.
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Diels–Alder reactions of enantiopure [(1S)-Isoborneol-10-sulfinyl]- and [(1S-exo)-2-bornylsulfinyl]vinylcyclohexenes with maleimides
Tetrahedron: Asymmetry, 1999Co-Authors: Maria C. Aversa, Anna Barattucci, Paola Bonaccorsi, Placido Giannetto, Francesco Nicolò, Simona RizzoAbstract:Abstract Uncatalyzed cycloadditions of enantiopure [(1 S )-Isoborneol-10-sulfinyl]- and [(1 S - exo )-2-bornylsulfinyl]vinylcyclohexenes with N -phenylmaleimide occur with good facial diastereoselectivity, controlled by the sulfur configuration, even if the extent of this stereoselection appears influenced by the structural features of the terpene residue directly linked to the sulfoxide moiety. Complete endo diastereoselectivity is observed in LiClO 4 catalyzed cycloadditions of ( R S )-1-{1-[(1 S )-Isoborneol-10-sulfinyl]- and ( S S )-1-{1-[(1 S-exo )-2-bornylsulfinyl]vinyl}cyclohexenes 4 and 5 , respectively. The Diels–Alder reactivity of 5 and ( S S , E )-1-{2-[(1 S-exo )-2-bornylsulfinyl]vinyl}cyclohexene 7 , with the chiral auxiliary being in a different position with respect to the diene moiety, is also compared, and the results obtained comfirm that 1-sulfinyldienes are less reactive than 2-sulfinyldienes. SnCl 4 catalyzed cycloaddition of 7 with N -methylmaleimide is also performed.
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First hetero-diels-alder reaction of an enantiopure 2-sulfinylbuta-1, 3-diene: mild and effective stereocontrolled synthesis of pyranoid derivatives
Tetrahedron: Asymmetry, 1997Co-Authors: Maria C. Aversa, Anna Barattucci, Paola Bonaccorsi, Giuseppe Bruno, Placido Giannetto, Manuela PanzalortoAbstract:Abstract LiClO 4 catalyzed cycloaddition of (R S ,E)-3-[(1S)-Isoborneol-10-sulfinyl]-1-methoxybuta-1,3-diene 1 with ethyl glyoxalate occurred with good endo and facial diastereoselectivities to give (2R,6S,R S )-6-ethoxycarbonyl-4-[(1S)-Isoborneol-10-sulfinyl]-2-methoxy-5,6-dihydro-2H-pyran 2 as the main product, easily isolated as crystalline material in high yield.
Paola Bonaccorsi - One of the best experts on this subject based on the ideXlab platform.
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Synthesis of Enantiomerically Pure Bis‐Sulfinyl Substituted Phenylene Ethynylenes
Helvetica Chimica Acta, 2014Co-Authors: Anna Barattucci, Maria C. Aversa, Elisa Deni, Teresa Papalia, Paola BonaccorsiAbstract:The stereoselective and efficient monoaddition of transient [(1S,2R,4R)-2-hydroxy-7,7-dimethylbicyclo[2.2.1]hept-1-yl]methanesulfenic (=(1S)-Isoborneol-10-sulfenic) acid to isomeric diethynylbenzenes affords {1-[(1S)-Isoborneol-10-sulfinyl]ethenyl}ethynylbenzenes. Their enantiomerically pure (RS)-epimers are involved in a Cu-free Sonogashira coupling with 1,4-diiodo-2,5-dimethoxybenzene to give C2-symmetric bis-sulfinyl phenylene ethynylenes, stimulating prototypes of new sulfurated chiral architectures that can find application as chelating agents.
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diels alder reactions of enantiopure 1s Isoborneol 10 sulfinyl and 1s exo 2 bornylsulfinyl vinylcyclohexenes with maleimides
Tetrahedron-asymmetry, 1999Co-Authors: Maria C. Aversa, Anna Barattucci, Paola Bonaccorsi, Placido Giannetto, Francesco Nicolò, Simona RizzoAbstract:Abstract Uncatalyzed cycloadditions of enantiopure [(1 S )-Isoborneol-10-sulfinyl]- and [(1 S - exo )-2-bornylsulfinyl]vinylcyclohexenes with N -phenylmaleimide occur with good facial diastereoselectivity, controlled by the sulfur configuration, even if the extent of this stereoselection appears influenced by the structural features of the terpene residue directly linked to the sulfoxide moiety. Complete endo diastereoselectivity is observed in LiClO 4 catalyzed cycloadditions of ( R S )-1-{1-[(1 S )-Isoborneol-10-sulfinyl]- and ( S S )-1-{1-[(1 S-exo )-2-bornylsulfinyl]vinyl}cyclohexenes 4 and 5 , respectively. The Diels–Alder reactivity of 5 and ( S S , E )-1-{2-[(1 S-exo )-2-bornylsulfinyl]vinyl}cyclohexene 7 , with the chiral auxiliary being in a different position with respect to the diene moiety, is also compared, and the results obtained comfirm that 1-sulfinyldienes are less reactive than 2-sulfinyldienes. SnCl 4 catalyzed cycloaddition of 7 with N -methylmaleimide is also performed.
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Enantiopure sulfinylthiopyrans and related compounds from alkylsulfinylbuta-1,3-dienes
Tetrahedron: Asymmetry, 1999Co-Authors: Maria C. Aversa, Anna Barattucci, Paola Bonaccorsi, Placido Giannetto, Bianca F. Bonini, Francesco NicolòAbstract:Uncatalyzed and LiClO4 catalyzed cycloadditions of (RS)-1-{1-[(1S)-Isoborneol-10-sulfinyl]vinyl}cyclohexene 1 and (RS,E)-3-[(1S)-Isoborneol-10-sulfinyl]-1-methoxybuta-1,3-diene 2 with di(p-tolyl)- and di(p-anisyl)thioketones 3 and 4 occur with complete regioselectivity. The lack of facial diastereoselectivity, observed in the cycloadditions of 1 with 3 or 4, appears to be a consequence of the sterical features of both diene and dienophile which, in the transition states, make the topological differentiation induced by the presence of the alkylsulfinyl group as chiral auxiliary uninfluential. No significant improvement in diastereoselectivity is observed in the LiClO4 catalyzed reactions, but the obtained enantiopure cycloadducts are easily separated by column chromatography and isolated in high yields. © 1999 Elsevier Science Ltd. All rights reserved.
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Diels–Alder reactions of enantiopure [(1S)-Isoborneol-10-sulfinyl]- and [(1S-exo)-2-bornylsulfinyl]vinylcyclohexenes with maleimides
Tetrahedron: Asymmetry, 1999Co-Authors: Maria C. Aversa, Anna Barattucci, Paola Bonaccorsi, Placido Giannetto, Francesco Nicolò, Simona RizzoAbstract:Abstract Uncatalyzed cycloadditions of enantiopure [(1 S )-Isoborneol-10-sulfinyl]- and [(1 S - exo )-2-bornylsulfinyl]vinylcyclohexenes with N -phenylmaleimide occur with good facial diastereoselectivity, controlled by the sulfur configuration, even if the extent of this stereoselection appears influenced by the structural features of the terpene residue directly linked to the sulfoxide moiety. Complete endo diastereoselectivity is observed in LiClO 4 catalyzed cycloadditions of ( R S )-1-{1-[(1 S )-Isoborneol-10-sulfinyl]- and ( S S )-1-{1-[(1 S-exo )-2-bornylsulfinyl]vinyl}cyclohexenes 4 and 5 , respectively. The Diels–Alder reactivity of 5 and ( S S , E )-1-{2-[(1 S-exo )-2-bornylsulfinyl]vinyl}cyclohexene 7 , with the chiral auxiliary being in a different position with respect to the diene moiety, is also compared, and the results obtained comfirm that 1-sulfinyldienes are less reactive than 2-sulfinyldienes. SnCl 4 catalyzed cycloaddition of 7 with N -methylmaleimide is also performed.
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First hetero-diels-alder reaction of an enantiopure 2-sulfinylbuta-1, 3-diene: mild and effective stereocontrolled synthesis of pyranoid derivatives
Tetrahedron: Asymmetry, 1997Co-Authors: Maria C. Aversa, Anna Barattucci, Paola Bonaccorsi, Giuseppe Bruno, Placido Giannetto, Manuela PanzalortoAbstract:Abstract LiClO 4 catalyzed cycloaddition of (R S ,E)-3-[(1S)-Isoborneol-10-sulfinyl]-1-methoxybuta-1,3-diene 1 with ethyl glyoxalate occurred with good endo and facial diastereoselectivities to give (2R,6S,R S )-6-ethoxycarbonyl-4-[(1S)-Isoborneol-10-sulfinyl]-2-methoxy-5,6-dihydro-2H-pyran 2 as the main product, easily isolated as crystalline material in high yield.
James D. White - One of the best experts on this subject based on the ideXlab platform.
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Organic Syntheses - (2S)‐(−)‐3‐exo‐(Dimethylamino)Isoborneol [(2S)‐(−)‐DAIB]
Organic Syntheses, 2003Co-Authors: James D. White, Duncan J. Wardrop, Kurt F. Sundermann, Christopher E. Neipp, Stephen F. MartinAbstract:(2S)-(−)-3-exo-(Dimethylamino)Isoborneol, [(2S)-(−)-DAIB] R (−)-Camphorquinone 1 I (2S)-(−)-3-exo-AminoIsoborneol 2 (1R,2S,6R,7S)-1,10,10-Trimethyl-4-oxo-5-aza-3-oxatricyclo [5.2.1.0] decone 3 N-methyl-(1R,2S,6R,7S)-1,10,10-trimethyl-4-oxo-5-aza-3-oxatricyclo [5.2.1.0] decone 4 P (2S)-(−)-3-(−)-exo-(Dimethylamino)Isoborneol 5 Keywords: amines (and salts), aliphatic; alcohols and diols, substituted; reduction, CN CH2NH2; annulation, heterocyclic-[5]; heterocycles, five-membered, one nitrogen, one oxygen; alkylation, N-alkylation; acylation (including formylation and Friedel-Crafts reactions); alkylation, N-alkylation; heterocycles, five-membered, one nitrogen, one oxygen; reduction, miscellaneous; amines (and salts), aliphatic; alcohols and diols, substituted; DAIB, decomposition in air
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2s 3 exo dimethylamino Isoborneol 2s daib
Organic Syntheses, 2003Co-Authors: James D. White, Duncan J. Wardrop, Kurt F. Sundermann, Christopher E. Neipp, Stephen F. MartinAbstract:(2S)-(−)-3-exo-(Dimethylamino)Isoborneol, [(2S)-(−)-DAIB] R (−)-Camphorquinone 1 I (2S)-(−)-3-exo-AminoIsoborneol 2 (1R,2S,6R,7S)-1,10,10-Trimethyl-4-oxo-5-aza-3-oxatricyclo [5.2.1.0] decone 3 N-methyl-(1R,2S,6R,7S)-1,10,10-trimethyl-4-oxo-5-aza-3-oxatricyclo [5.2.1.0] decone 4 P (2S)-(−)-3-(−)-exo-(Dimethylamino)Isoborneol 5 Keywords: amines (and salts), aliphatic; alcohols and diols, substituted; reduction, CN CH2NH2; annulation, heterocyclic-[5]; heterocycles, five-membered, one nitrogen, one oxygen; alkylation, N-alkylation; acylation (including formylation and Friedel-Crafts reactions); alkylation, N-alkylation; heterocycles, five-membered, one nitrogen, one oxygen; reduction, miscellaneous; amines (and salts), aliphatic; alcohols and diols, substituted; DAIB, decomposition in air
