About: Benzo[d]imidazole and Aliphatic alpha-Amino Acid Derived Primary Amines in Asymmetric Aldol Reaction     Goto   Sponge   NotDistinct   Permalink

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  • Starting from essential alfa-amino acids, four new benzo[d]imidazole and alkyl chain substituted primary amines were synthesized. The reaction sequence involves activation of the Boc-amino acid carboxylic acid, reaction with o-phenylenediamine and subsequent cyclization to benzo[d]imidazole. N-Methylation and final Boc group removal afforded four new primary amines. The synthesized amines were preliminarily applied as organocatalysts in asymmetric version of the aldol reaction between 4-nitrobenzaldehyde and acetone/cyclohexanone achieving chemical yields 40-64 % and ee and de up to 65 and 96 %, respectively.
  • Starting from essential alfa-amino acids, four new benzo[d]imidazole and alkyl chain substituted primary amines were synthesized. The reaction sequence involves activation of the Boc-amino acid carboxylic acid, reaction with o-phenylenediamine and subsequent cyclization to benzo[d]imidazole. N-Methylation and final Boc group removal afforded four new primary amines. The synthesized amines were preliminarily applied as organocatalysts in asymmetric version of the aldol reaction between 4-nitrobenzaldehyde and acetone/cyclohexanone achieving chemical yields 40-64 % and ee and de up to 65 and 96 %, respectively. (en)
Title
  • Benzo[d]imidazole and Aliphatic alpha-Amino Acid Derived Primary Amines in Asymmetric Aldol Reaction
  • Benzo[d]imidazole and Aliphatic alpha-Amino Acid Derived Primary Amines in Asymmetric Aldol Reaction (en)
skos:prefLabel
  • Benzo[d]imidazole and Aliphatic alpha-Amino Acid Derived Primary Amines in Asymmetric Aldol Reaction
  • Benzo[d]imidazole and Aliphatic alpha-Amino Acid Derived Primary Amines in Asymmetric Aldol Reaction (en)
skos:notation
  • RIV/00216275:25310/14:39897795!RIV15-MSM-25310___
http://linked.open...avai/riv/aktivita
http://linked.open...avai/riv/aktivity
  • I, S
http://linked.open...iv/cisloPeriodika
  • 4
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  • 5090
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  • RIV/00216275:25310/14:39897795
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  • asymmetric aldolization; amino acid; Benzodimidazole (en)
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  • DE - Spolková republika Německo
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  • [15E0A2FDC19A]
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  • 25
http://linked.open...iv/tvurceVysledku
  • Bureš, Filip
  • Drabina, Pavel
  • Mohite, Pravinkumar Hansraj
http://linked.open...ain/vavai/riv/wos
  • 000331462000005
issn
  • 0936-5214
number of pages
http://bibframe.org/vocab/doi
  • 10.1055/s-0033-1340598
http://localhost/t...ganizacniJednotka
  • 25310
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