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Asymmetric henry reaction catalyzed by novel chiral bioxazolines from tartaric acid
Ravichandran Vasanthan,
Published in
2012
Volume: 44
   
Issue: 15
Pages: 2455 - 2462
Abstract
Novel C 2-symmetric chiral bioxazolines were synthesized in good yields by the fusion of optically active acids with a tartaric acid derivative. Complexes of these products with copper(II) acetate monohydrate were found to be excellent catalysts for the Henry reaction, giving various nitro alcohols in very good yields and up to 84% enantiomeric excess. Although only five-membered chelation is possible with these ligands, they give better enantioselectivities than other bioxazoline ligands that undergo similar coordination. © Georg Thieme Verlag Stuttgart · New York.
About the journal
JournalSynthesis (Germany)
ISSN00397881
Open AccessNo
Concepts (37)
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    Aldol reactions
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    Asymmetric catalysis
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    BIOXAZOLINE LIGANDS
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    Enantiomeric excess
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    HENRY REACTIONS
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    Heterocyclic compound
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    Nitro compounds
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    OPTICALLY ACTIVE
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    TARTARIC ACID DERIVATIVES
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    Tartaric acids
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    Alcohols
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    Catalysis
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    Copper compounds
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    Ligands
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    2,2' BIS(2 NAPHTHYLMETHYL) 4,4',5,5' TETRAHYDRO 4,4' BI 1,3 OXAZOLE
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    2,2' BIS[1 (4 ISOBUTYLPHENYL)ETHYL] 4,4',5,5' TETRAHYDRO 4,4' BI 1,3 OXAZOLE
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    2,2' BIS[1 (6 METHOXY 2 NAPHTHYL)ETHYL] 4,4',5,5' TETRAHYDRO 4,4' BI 1,3 OXAZOLE
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    Alcohol
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    BIOXAZOLINE DERIVATIVE
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    Copper acetate
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    N,N' [1,4 BIS(BENZYLOXY)BUTANE 2,3 DIYL]BIS[2 (4 ISOBUTYLPHENYL)PROPANAMIDE]
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    N,N' [1,4 BIS(BENZYLOXY)BUTANE 2,3 DIYL]BIS[2 (6 METHOXY 2 NAPHTHYL)PROPANAMIDE]
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    N,N' [1,4 DIHYDROXYBUTANE 2,3 DIYL]BIS[2 (2 NAPHTHYL)ACETAMIDE]
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    N,N' [1,4 DIHYDROXYBUTANE 2,3 DIYL]BIS[2 (4 ISOBUTYLPHENYL)PROPANAMIDE]
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    N,N' [1,4 DIHYDROXYBUTANE 2,3 DIYL]BIS[2 (6 METHOXY 2 NAPHTHYL)PROPANAMIDE]
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    Oxazoline derivative
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    TARTARIC ACID DERIVATIVE
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    Unclassified drug
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    Article
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    Catalyst
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    Chelation
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    Chemical reaction
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    Chirality
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    Enantiomer
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    Enantioselectivity
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    HENRY REACTION
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    Reaction analysis