Atroposelektywna synteza naturalnych chiralnych osiowo związków biarylowych. Część 1

Kołodziejska, R.; Tafelska-Kaczmarek, A.; Studzińska, R.

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Tytuł artykułu

Atroposelektywna synteza naturalnych chiralnych osiowo związków biarylowych. Część 1

Autorzy

Kołodziejska R. , Tafelska-Kaczmarek A. , Studzińska R.

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Warianty tytułu

Atroposelective synthesis of natural axially chiral biaryl compounds. Part 1

Języki publikacji

Abstrakty

In early twentieth century, it was already known that chemical compounds might be chiral without containing the chiral atoms. The presence of the stereogenic center is a sufficient but not necessary condition that the molecule appears in two forms which are mirror images. In certain cases, the limit of free rotation in the molecule may result in asymmetry, e.g. inhibition of rotation around single bond leads to axial isomers. This is the kind of conformational isomerism, which according to the nomenclature is called atropisomerism [1, 2]. The most often optically active molecules without stereogenic atoms, possessing an axial chirality are biaryls, which are commonly found in nature. In most cases, pharmacological activity of biaryls is associated with the presence of axial chirality (Figs 1, 2; Scheme 1) [1–14]. Generally chiral biaryls are divided into bridged biaryls (Scheme 4–6) [15–24], and biaryls, which do not contain the additional ring (Scheme 2, 3) [25–33]. The thermal stability of both enantiomeric/diastereomeric forms is an essential precondition for atropisomerism. For a given temperature, conformationally stable isomers may coexist when their a half-life is at least 1000 s, which gives the minimum energy barrier of 93 kJ mol^–1 at 300 K. Chiral biaryls can be achieved by either desymmetrization of stable but achiral biaryls by modifying one of the groups on the aromatic moiety (Scheme 7–9) [1, 34, 35], or by dynamic kinetic resolution of racemic mixtures of the conformationally unstable chiral substrates. The synthesis of the chirally stable biaryls from the chiral labile substrates is most frequently the result of the extra substituent addition (Scheme 10) [36], and formation or cleavage of a bridge (Scheme 11–16) [37–54]. The axially chiral biaryls can also be obtained in the atroposelective transformation of the alkyl substituent of the arene ring into a second aromatic ring in the presence of an organometallic catalyst (Scheme 17, 18) [55, 56].

Słowa kluczowe

mostkowane biaryle otwarto-łańcuchowe biaryle atropoizomeryzacja synteza atroposelektywna chiralne osiowo biaryle

natural axially chiral biaryl compounds bridged biaryls unbridged biaryls atropoisomerization atroposelective synthesis axially chiral biaryls

Wydawca

Polskie Towarzystwo Chemiczne

Czasopismo

Wiadomości Chemiczne

Rocznik

2017

Tom

[Z] 71, 3-4

Strony

177--197

Opis fizyczny

Bibliogr. 56 poz., schem.

Twórcy

autor

Kołodziejska R.

Katedra i Zakład Biochemii, Collegium Medicum w Bydgoszczy, UMK Toruń ul. Karłowicza 24, 85-092 Bydgoszcz

autor

Tafelska-Kaczmarek A.

Katedra Chemii Organicznej, Wydział Chemii, UMK Toruń ul. Gagarina 7, 87-100 Toruń

autor

Studzińska R.

Katedra i Zakład Chemii Organicznej, Collegium Medicum w Bydgoszczy, UMK Toruń, ul. A. Jurasza 2, 85-089 Bydgoszcz

Bibliografia

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Uwagi

Opracowanie ze środków MNiSW w ramach umowy 812/P-DUN/2016 na działalność upowszechniającą naukę (zadania 2017).

Typ dokumentu

Bibliografia

Identyfikator YADDA

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