B-hydroxyamide derivates of b-cyclodextrin as organocatalysts for enantioselective reduction of prochiral ketones

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F46747885%3A24620%2F12%3A%230000084" target="_blank" >RIV/46747885:24620/12:#0000084 - isvavai.cz</a>

Výsledek na webu

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DOI - Digital Object Identifier

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Jazyk výsledku

angličtina

Název v původním jazyce

B-hydroxyamide derivates of b-cyclodextrin as organocatalysts for enantioselective reduction of prochiral ketones

Popis výsledku v původním jazyce

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.

Název v anglickém jazyce

B-hydroxyamide derivates of b-cyclodextrin as organocatalysts for enantioselective reduction of prochiral ketones

Popis výsledku anglicky

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.

Druh

O - Ostatní výsledky

CEP obor

CC - Organická chemie

OECD FORD obor

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Projekt

Výsledek vznikl pri realizaci vícero projektů. Více informací v záložce Projekty.

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Rok uplatnění

2012

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů