Preparation of 3,3'-bis(1-benzyl-1,4-dihydro-3-pyridyl-carbonylaminomethyl)-2,2'-dihydroxy-1,1'-binaphthyl, a potential NAD(P)H model compound.
Item
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Title
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Preparation of 3,3'-bis(1-benzyl-1,4-dihydro-3-pyridyl-carbonylaminomethyl)-2,2'-dihydroxy-1,1'-binaphthyl, a potential NAD(P)H model compound.
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Identifier
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AAI9510687
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identifier
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9510687
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Creator
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Lutz, Patricia M.
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Contributor
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Adviser: Howard Haubenstock
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Date
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1994
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Language
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English
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Publisher
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City University of New York.
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Subject
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Chemistry, Organic
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Abstract
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The design, synthesis, and characterization of the title compound, a novel bis-1,4-dihydronicotinamide possessing the 2,2{dollar}\sp\prime{dollar}-dihydroxy-1,1{dollar}\sp\prime{dollar}-binaphthyl as the chiral source with C{dollar}\sb2{dollar} symmetry rather than a chiral center, is described. The synthesis involved the condensation of nicotinoyl chloride with newly prepared chiral bisnicotinamide, 3,3{dollar}\sp\prime{dollar}-bis({dollar}3{dollar} -pyridylcarbonylaminomethyl)-2,2{dollar}\sp\prime{dollar}-dihydroxy-{dollar}1{dollar},1{dollar}\sp\prime{dollar}-binaphthyl, followed by quaternization with alkyl halide, and then reduction by {dollar}\rm Na\sb2S\sb2O\sb4{dollar}. The synthesis and characterization of the new binaphthyls (intermediates) 2,2{dollar}\sp\prime{dollar}-dihydroxy-{dollar}1{dollar},1{dollar}\sp\prime{dollar}-binaphthyl-3,3{dollar}\sp\prime{dollar}-dicarboxamide, 3,3{dollar}\sp\prime{dollar}-bis(aminomethyl)-{dollar}2{dollar},2{dollar}\sp\prime{dollar}-dihydroxy-1,1{dollar}\sp\prime{dollar}-binaphthyl, and 3,3{dollar}\sp\prime{dollar}-bis(3-pyridylcarbonylaminomethyl)-{dollar}2{dollar},2{dollar}\sp\prime{dollar}-dihydroxy-1,1{dollar}\sp\prime{dollar}-binaphthyl is also described.;In another series of experiments, acetophenone was found to be reduced in 4-24% enantiomeric excess by the chiral hydride reagent formed by the complexation of LiAlH{dollar}\sb4{dollar}, (R)-({dollar}-{dollar})-3,3-dimethyl-1,2-butanediol and achiral alcohols.
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Type
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dissertation
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Source
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PQT Legacy CUNY.xlsx
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degree
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Ph.D.
