Chiralne katalizatory organiczne w asymetrycznej reakcji Michaela

• Autorzy: Albrecht Ł. , Krawczyk H.

Warianty tytułu

EN

Chiral organocatalysts in asymmetric Michael reaction

• Języki publikacji: PL

Abstrakty

EN

In marked contrast to enantioselective Michael reactions promoted by chiral Lewis acids, organocatalytic Michael reactions have not been used as standard transformation in organic chemistry until quite recently. During the past few years chiral organocatalysts have emerged as a broadly applicable class of catalysts for enantioselective Michael reaction. This review summarizes these advances emphasizing the structural and mechanistic features that contribute to high enantioselectivity in organocatalytic Michael reactions. The first part of this review deals with the development of covalent catalysis in organocatalytic asymmetric Michael reactions. To date, several chiral secondary amines have been employed to promote formation of electron-rich enamines from enolizable aldehydes and ketones, which then react with various ?,?-unsaturated electrophiles to afford products [7-24]. In contrast, chiral imidazolidinones and diarylprolinol ethers are most often used to activate ?,?-unsaturated carbonyl compounds by forming electron-deficient iminium ions, which render the ?-carbon more electrophilic then their carbonyl precursors for nucleophilic attack [2a, 7, 25-34]. The second part of this review documents the development of non-covalent catalysis [35-64]. In this regard, chiral Bronstedt bases [35-39], chiral phase-transfer catalysts [40-49] and chiral hydrogen-bond donors [50-64] have emerged in the past few years as readily accessible organocatalysts of asymmetric Michael reaction. The most efficient catalysts such as cinchona alkaloids and their derivatives, quaternary ammonium salts obtained from cinchona alkaloids and chiral thiourea derivatives, respectively are revived and the modes of actions are discussed. Furthermore, the major developments of organocatalytic asymmetric Michael reactions are also reviewed.

Słowa kluczowe

PL

organokataliza; reakcja Michaela; synteza asymetryczna

EN

organocatalysis; Michael reaction; asymmetric synthesis

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Wiadomości Chemiczne
• Rocznik: 2009
• Tom: [Z] 63, 5-6
• Strony: 391--436
• Opis fizyczny: bibliogr. 64 poz., wykr.

Twórcy

autor

Albrecht Ł.

autor

Krawczyk H.

• Instytut Chemii Organicznej, Wydział Chemiczny, Politechnika Łódzka, ul. Żeromskiego 116, 90-924 Łódź,

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