About: B-hydroxyamide derivates of b-cyclodextrin as organocatalysts for enantioselective reduction of prochiral ketones     Goto   Sponge   NotDistinct   Permalink

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  • Cyclodextrins (CDs) are macrocyclic compounds with cone-shaped cavity formed by a-1,4-linked D-glucopyranose units. CDs are often used as nanoreactors or organocatalysts for various reactions.1 A recent study also showed that series of b-hydroxyamides derived from chiral alkylamino alcohols could be successfully used in asymmetric borane reduction of prochiral ketones.2 In this respect we tried out if b-hydroxyamide derivatives of b-cyclodextrin will enhance the enantioselectivity of the reduction. b-Hydroxyamide derivatives of b-cyclodextrin (3a and 3b) were synthesized via 6I-amino-6I-deoxy-b-cyclodextrin 2 (Scheme 1). It is noteworthy to mention that none of the steps in the synthesis requires chromatography. Only crystallizations were used. Catalytic activity of compounds 3a and 3b in asymmetric borane reduction of prochiral ketones is currently investigated.
  • Cyclodextrins (CDs) are macrocyclic compounds with cone-shaped cavity formed by a-1,4-linked D-glucopyranose units. CDs are often used as nanoreactors or organocatalysts for various reactions.1 A recent study also showed that series of b-hydroxyamides derived from chiral alkylamino alcohols could be successfully used in asymmetric borane reduction of prochiral ketones.2 In this respect we tried out if b-hydroxyamide derivatives of b-cyclodextrin will enhance the enantioselectivity of the reduction. b-Hydroxyamide derivatives of b-cyclodextrin (3a and 3b) were synthesized via 6I-amino-6I-deoxy-b-cyclodextrin 2 (Scheme 1). It is noteworthy to mention that none of the steps in the synthesis requires chromatography. Only crystallizations were used. Catalytic activity of compounds 3a and 3b in asymmetric borane reduction of prochiral ketones is currently investigated. (en)
Title
  • B-hydroxyamide derivates of b-cyclodextrin as organocatalysts for enantioselective reduction of prochiral ketones
  • B-hydroxyamide derivates of b-cyclodextrin as organocatalysts for enantioselective reduction of prochiral ketones (en)
skos:prefLabel
  • B-hydroxyamide derivates of b-cyclodextrin as organocatalysts for enantioselective reduction of prochiral ketones
  • B-hydroxyamide derivates of b-cyclodextrin as organocatalysts for enantioselective reduction of prochiral ketones (en)
skos:notation
  • RIV/46747885:24620/12:#0000084!RIV13-MSM-24620___
http://linked.open...avai/riv/aktivita
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  • P(ED0005/01/01), P(EE2.3.30.0024)
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  • 124893
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  • RIV/46747885:24620/12:#0000084
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  • Cyclodextrin, organocatalysis, borane, reduction (en)
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  • [017EE01877DD]
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  • Řezanka, Michal
  • Stibor, Ivan
http://localhost/t...ganizacniJednotka
  • 24620
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