Prolina : pospolity aminokwas wyjątkowy katalizator. Część III, Reakcja Mannicha

• Autorzy: Studzińska R. , Karczmarska-Wódzka A. , Wróblewski M. , Kołodziejska R. , Dramiński M.

Warianty tytułu

EN

Proline as a common amino acid and an exceptional catalyst. Part III, Mannich reaction

• Języki publikacji: PL

Abstrakty

EN

Mannich reaction occuring among ketone, aldehyde, and amine is one of the ways of a synthesis of biologically active compounds. Reactions of this type were carried out in the presence of different catalysts [3–10], however in recent years a lot of attention has been paid to enantioselective Mannich reaction catalyzed with proline. Such reactions were carried out with the use of different compounds containing carbonyl group and the most frequently used amine was p-anisidine. The advantage of the use of p-anisidine is a possibility of conducting the direct Mannich reaction (Scheme 3). In this way β-amino ketones (Tab. 1, 2, 4) [15, 18–20, 23, 24], α-hydroxy-β-amino ketones (Tab. 3) [15, 22], and β-amino alcohols (Tab. 5, 6) [25, 26] were obtained. A possibility of syntheses of β-amino sugars and α-amino acids with their derivatives (Tab. 7) [28, 29] is worth noticing. In a great number of described reactions, the products were obtained with satisfactory yield and enantiomeric excess. Taking into consideration the difficulty of a removal of p-hydroxyphenyl group which protects amine group in the resulting products, the attempts of using different amine compounds in Mannich reactions catalyzed with proline were undertaken. The use of amines blocked by tert-butoxycarbonyl group (Boc) enabled to obtain the products with high yield and ee values (Tab. 12–15) [35–38]. However in the case of the use of Boc the reaction must be carried out in an indirect way (it is necessary to prepare imine blocked by Boc earlier).

Słowa kluczowe

PL

prolina; reakcja Mannicha; synteza asymetryczna

EN

proline; Mannich reaction; asymmetric synthesis

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Wiadomości Chemiczne
• Rocznik: 2014
• Tom: [Z] 68, 1-2
• Strony: 21--48
• Opis fizyczny: Bibliogr. 39 poz., schem., tab.

Twórcy

autor

Studzińska R.

• Katedra i Zakład Chemii Ogólnej Uniwersytetu Mikołaja Kopernika, Collegium Medicum w Bydgoszczy, ul. Dębowa 3, 85-626 Bydgoszcz

autor

Karczmarska-Wódzka A.

• Katedra i Zakład Chemii Ogólnej Uniwersytetu Mikołaja Kopernika, Collegium Medicum w Bydgoszczy, ul. Dębowa 3, 85-626 Bydgoszcz

autor

Wróblewski M.

• Katedra i Zakład Chemii Ogólnej Uniwersytetu Mikołaja Kopernika, Collegium Medicum w Bydgoszczy, ul. Dębowa 3, 85-626 Bydgoszcz

autor

Kołodziejska R.

• Katedra i Zakład Chemii Ogólnej Uniwersytetu Mikołaja Kopernika, Collegium Medicum w Bydgoszczy, ul. Dębowa 3, 85-626 Bydgoszcz

autor

Dramiński M.

• Katedra i Zakład Chemii Ogólnej Uniwersytetu Mikołaja Kopernika, Collegium Medicum w Bydgoszczy, ul. Dębowa 3, 85-626 Bydgoszcz

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