Aldehydes use: Prins cyclization as a useful tool for formation of dihydropyranic and tetrahydropyranic structures.

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22310%2F20%3A43920602" target="_blank" >RIV/60461373:22310/20:43920602 - 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

Aldehydes use: Prins cyclization as a useful tool for formation of dihydropyranic and tetrahydropyranic structures.

Popis výsledku v původním jazyce

Dihydropyranic or tetrahydropyranic cycles occur in the structure of many biologically active compounds. The simplest and the most commonly used method of preparing such compounds is the so-called Prins cyclization. Prins cyclization is the reaction of an aldehyde with a homoallylic alcohol in the presence of an acid catalyst. Various catalysts were used and described for this particular reaction, and mentions of all types of acid catalysts may be found. Strong Lewis acid are the most often used, especially boron trifluoride etherate (other used Lewis acids are, e.g., metal triflates, iodine, and others). From Brønsted acids especially acids containing sulfuric group (e.g., sulfuric acid, p toluenesulfonic acid, Amberlyst 15, etc.) are described. Heterogenized homogeneous acids are also used in Prins cyclization using advantages of both arrangements – high and defined selectivity, simple separation from the reaction mixture and possible reuse. The use of solid acids (e.g., zeolites, clays, metal oxides) is also possible, but the mechanism is more complicated in this case because both acid types participate in the reaction. This chapter offers an overview of the influence of different acids types on the reaction course and selectivity of Prins cyclization of chosen aldehydes and homoallylic alcohols.

Název v anglickém jazyce

Aldehydes use: Prins cyclization as a useful tool for formation of dihydropyranic and tetrahydropyranic structures.

Popis výsledku anglicky

Dihydropyranic or tetrahydropyranic cycles occur in the structure of many biologically active compounds. The simplest and the most commonly used method of preparing such compounds is the so-called Prins cyclization. Prins cyclization is the reaction of an aldehyde with a homoallylic alcohol in the presence of an acid catalyst. Various catalysts were used and described for this particular reaction, and mentions of all types of acid catalysts may be found. Strong Lewis acid are the most often used, especially boron trifluoride etherate (other used Lewis acids are, e.g., metal triflates, iodine, and others). From Brønsted acids especially acids containing sulfuric group (e.g., sulfuric acid, p toluenesulfonic acid, Amberlyst 15, etc.) are described. Heterogenized homogeneous acids are also used in Prins cyclization using advantages of both arrangements – high and defined selectivity, simple separation from the reaction mixture and possible reuse. The use of solid acids (e.g., zeolites, clays, metal oxides) is also possible, but the mechanism is more complicated in this case because both acid types participate in the reaction. This chapter offers an overview of the influence of different acids types on the reaction course and selectivity of Prins cyclization of chosen aldehydes and homoallylic alcohols.

Druh

C - Kapitola v odborné knize

CEP obor

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OECD FORD obor

10401 - Organic chemistry

Projekt

<a href="/cs/project/LO1613" target="_blank" >LO1613: Výzkum nových materiálů pro chemický průmysl</a><br>

Návaznosti

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

Rok uplatnění

2020

Kód důvěrnosti údajů

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

Název knihy nebo sborníku

Advances in Chemistry Research. Volume 63

ISBN

978-1-5361-8301-6

Počet stran výsledku

56

Strana od-do

131-174

Počet stran knihy

245

Název nakladatele

Nova Science Publishers, Inc.

Místo vydání

New York

Kód UT WoS kapitoly

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