Asymetryczna reakcja aldolowa: część II - katalityczna asymetryczna reakcja aldolowa w środowisku wodnym

• Autorzy: Paradowska J. , Rogozińska M. , Młynarski J.

Warianty tytułu

EN

Asymmetric aldol reaction: part II - catalytic asymmetric aldol reaction in aqueous media

• Języki publikacji: PL

Abstrakty

EN

Asymmetric organometallic and organocatalytic processes in aqueous systems are currently of great interest. A few years ago, only a few practitioners studied the subject; now organic reactions in water have become one of the most exciting research areas. Nature has perfected the stereospecific aldol reaction by using aldolase enzymes. While virtually all the biochemical aldol reactions use unmodified donor and acceptor carbonyls and take place under catalytic control in an aqueous environment, the chemical domain of the aldol addition has mostly relied on prior transformation of carbonyl substrates, and the whole process traditionally is carried out in anhydrous solvents. The area of asymmetric aldol reactions in water has received much attention recently in light of the perception of both its green chemistry advantages and its analogy to eon-perfected enzyme catalysis. Only recently catalytic asymmetric reactions promoted by water-compatible Lewis acids with chiral ligands have been developed; most Lewis acids are not stable in water. Seminal work by List, Lerner, and Barbas on the intermolecular proline-catalyzed direct asymmetric aldol reaction opened a new platform for designing metal-free asymmetric catalysts, although their application was initially limited to organic solvents. Most recently, the challenge of developing efficient aqueous-phase organocatalytic processes has also been tackled. Recent progress in the area initiated constructive discussion on the role and practical merits of water as a solvent. This article describes recent developments in this area.

Słowa kluczowe

PL

bezpośrednia reakcja aldolowa; reakcja aldolowa asymetryczna; reakcja Mukaiyamy; woda; kwasy Lewisa; aminokwasy; organokataliza; synteza totalna

EN

direct aldol reaction; asymmetric aldol reaction; Mukaiyama reaction; water; Lewis acids; amino acids; organocatalysis; total synthesis

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Wiadomości Chemiczne
• Rocznik: 2010
• Tom: [Z] 64, 7-8
• Strony: 599--627
• Opis fizyczny: Bibliogr. 53 poz., schem., tab.

Twórcy

autor

Paradowska J.

autor

Rogozińska M.

autor

Młynarski J.

• Instytut Chemii Organicznej Polskiej Akademii Nauk ul. Kasprzaka 44/52, 01-224, Warszawa,

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