Prolina : pospolity aminokwas wyjątkowy katalizator. Część III, Reakcja Mannicha Proline as a common amino acid and an exceptional catalyst. Part III, Mannich reaction
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).
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