کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
1347670 980320 2008 8 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Synthesis of camphorsulfonamide-based quinoline ligands and their N-oxides: first use in the enantioselective addition of organozinc reagents to aldehydes
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی معدنی
پیش نمایش صفحه اول مقاله
Synthesis of camphorsulfonamide-based quinoline ligands and their N-oxides: first use in the enantioselective addition of organozinc reagents to aldehydes
چکیده انگلیسی

The preparation of several camphorsulfonamide-based quinoline derivatives and their N-oxides was accomplished via an indirect Friedländer synthesis using aminobenzylic alcohols and RuCl2(DMSO)4 as a catalyst. These ligands were tested in the enantioselective addition of dialkylzinc reagents to aldehydes, with enantiomeric excesses up to 96%. A similar protocol using triphenylborane and diethylzinc gave the corresponding phenylation process.

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N-Benzyl-(1S,12S)-15,15-dimethyl-3-azatetracyclo[10.2.1.0.2,11.04,9] pentadeca-2(11),3,5,7,9-pentaen-1-ylmethanesulfonamideC24H26N2O2SEe = 100%[α]D25=+76.9 (c 8.5 CHCl3)Source of chirality: (+)-10-Camphorsulfonyl chlorideAbsolute configuration: (1S, 12S)

N-Benzyl-(1S,16S)-19,19-dimethyl-3-azapentacyclo[14.2.1.0.4,13.05,10]nonadeca-2(15),3,5(10),6,8,11,13-heptaen-1-ylmethanesulfonamideC28H28N2O2SEe = 100%[α]D25=+28.0 (c 13.5 CHCl3)Source of chirality: (+)-10-Camphorsulfonyl chlorideAbsolute configuration: (1S, 16S)

N-(2-Dimethylaminoethyl)-(1S,12S)-15,15-dimethyl-3-azatetracyclo[10.2.1.0.2,1104,9]pentadeca-2(11),3,5,7,9-pentaen-1-ylmethanesulfonamideC21H29N3O2SEe = 100%[α]D25=+76.2 (c 1.0 CHCl3)Source of chirality: (+)-10-Camphorsulfonyl chlorideAbsolute configuration: (1S, 12S)

N-(2-Dimethylaminoethyl)-N-methyl-(1S,12S)-15,15-dimethyl-3-azatetracyclo[10.2.1.0.2,1104,9]pentadeca-2(11),3,5,7,9-pentaen-1-ylmethanesulfonamideC22H31N3O2SEe = 100%[α]D25=+17.0 (c 1.2 CHCl3)Source of chirality: (+)-10-Camphorsulfonyl chlorideAbsolute configuration: (1S, 12S)

N-{(1R,2R)-2-[(1S,12S)-15,15-Dimethyl-3-azatetracyclo[10.2.1.0.2,1104,9]pentadeca-2(11),3,5,7,9-pentaen-1-ylmethylsulfonamido]cyclohexyl}-(1S,12S)-15,15-dimethyl-3-azatetracyclo[10.2.1.0.2,1104,9]pentadeca-2(11),3,5,7,9-pentaen-1-ylmethanesulfonamideC40H48N4O4S2Ee = 100%[α]D25=+60.8 (c 1.1 CHCl3)Source of chirality: (+)-10-Camphorsulfonyl chloride and (1R,2R)-1,2-diaminocyclohexaneAbsolute configuration: (1R, 2R, 1′S, 12′S)

N-{(1R,2R)-2-[(1R,12R)-15,15-Dimethyl-3-azatetracyclo[10.2.1.0.2,1104,9]pentadeca-2(11),3,5,7,9-pentaen-1-ylmethylsulfonamido]cyclohexyl}-(1R,12R)-15,15-dimethyl-3-azatetracyclo[10.2.1.0.2,1104,9]pentadeca-2(11),3,5,7,9-pentaen-1-ylmethanesulfonamideC40H48N4O4S2Ee = 100%[α]D25=-67.2 (c 1.0 CHCl3)Source of chirality: (−)-10-Camphorsulfonyl chloride and (1R,2R)-1,2-diaminocyclohexaneAbsolute configuration: (1R, 2R, 1′R, 12′R)

N-{(1R,2S)-2-[(1S,12S)-15,15-Dimethyl-3-azatetracyclo[10.2.1.0.2,1104,9]pentadeca-2(11),3,5,7,9-pentaen-1-ylmethylsulfonamido]cyclohexyl}-(1S,12S)-15,15-dimethyl-3-azatetracyclo[10.2.1.0.2,1104,9]pentadeca-2(11),3,5,7,9-pentaen-1-ylmethanesulfonamideC40H48N4O4S2Ee = 100%[α]D25=+142.0 (c 1.0 CHCl3)Source of chirality: (+)-10-Camphorsulfonyl chlorideAbsolute configuration: (1R, 2R, 1′S, 12’S)

N-[(1R,2R)-2-(4-methylphenylsulfonamido)cyclo-hexyl]-(1S,12S)-15,15-dimethyl-3-azatetracyclo[10.2.1.0.2,1104,9]pentadeca-2(11),3,5,7,9-pentaen-1-ylmethanesulfonamideC30H37N3O4S2Ee = 100%[α]D25=-0.7 (c 1.6 CHCl3)Source of chirality: (+)-10-Camphorsulfonyl chloride and (1R,2R)-1,2-diaminocyclohexaneAbsolute configuration: (1R, 2R, 1′S, 12′S)

N-[(1R,2R)-2-(4-Trifluoromethylphenylsulfonamido)cyclohexyl]-(1S,12S)-15,15-dimethyl-3-azatetracyclo[10.2.1.0.2,1104,9]pentadeca-2(11),3,5,7,9-pentaen-1-ylmethanesulfonamideC30H34F3N3O4S2Ee = 100%[α]D25=-1.1 (c 1.0 CHCl3)Source of chirality: (+)-10-Camphorsulfonyl chloride and (1R,2R)-1,2-diaminocyclohexaneAbsolute configuration: (1R, 2R, 1′S, 12′S)

1-{(1R,2R)-2-[(1S,12S)-15,15-Dimethyl-3-olato-3-azoniatetracyclo[10.2.1.0.2,1104,9]pentadeca-2(11),3,5,7,9-pentaen-1-ylmethylsulfonamido]cyclohexylsulfamoylmethyl}-(1S,12S)-15,15-dimethyl-3-azoniatetracyclo[10.2.1.0.2,1104,9]pentadeca-2(11),3,5,7,9-pentaen-3-olateC40H48N4O6S2Ee = 100%[α]D25=-4.5 (c 1.1 CHCl3)Source of chirality: (+)-10-Camphorsulfonyl chloride and (1R,2R)-1,2-diaminocyclohexaneAbsolute configuration: (1R, 2R, 1′S, 12′S)

1-{(1R,2R)-2-[(1R,12R)-15,15-Dimethyl-3-olato-3-azoniatetracyclo[10.2.1.0.2,1104,9]pentadeca-2(11),3,5,7,9-pentaen-1-ylmethylsulfonamido]cyclohexylsulfamoylmethyl}-(1R,12R)-15,15-dimethyl-3-azoniatetracyclo[10.2.1.0.2,1104,9]pentadeca-2(11),3,5,7,9-pentaen-3-olateC40H48N4O6S2Ee = 100%[α]D25=+44.0 (c 1.0 CHCl3)Source of chirality: (−)-10-Camphorsulfonyl chloride and (1R,2R)-1,2-diaminocyclohexaneAbsolute configuration: (1R, 2R, 1′R, 12′R)

1-{(1R,2S)-2-[(1S,12S)-15,15-Dimethyl-3-olato-3-azoniatetracyclo[10.2.1.0.2,1104,9]pentadeca-2(11),3,5,7,9-pentaen-1-ylmethylsulfonamido]cyclohexylsulfamoylmethyl}-(1S,12S)-15,15-dimethyl-3-azoniatetracyclo[10.2.1.0.2,1104,9]pentadeca-2(11),3,5,7,9-pentaen-3-olateC40H48N4O6S2Ee = 100%[α]D25=-32.5 (c 1.1 CHCl3)Source of chirality: (+)-10-Camphorsulfonyl chlorideAbsolute configuration: (1R, 2R, 1′S, 12′S)

ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Tetrahedron: Asymmetry - Volume 19, Issue 22, 17 November 2008, Pages 2600–2607
نویسندگان
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