Abstract
Abstract Organocatalysis, that is the use of small organic molecules to catalyze organic transformations, has been included among the most successful concepts in asymmetric catalysis, and it has been used for the enantioselective construction of C–C, C–N, C–O, C–S, C–P and C–halide bonds. Since the seminal works in early 2000, the scientific community has been paying an ever-growing attention to the use of organocatalysts for the synthesis, with high yields and remarkable stereoselectivities, of optically active fine chemicals of interest for the pharmaceutical industry. A brief overview is here presented about the two main classes of substrate activation by the catalyst: covalent organocatalysis and non-covalent organocatalysis, with a more stringent focus on some recent outcomes in the field of the latter and of hydrogen bond-based catalysis. Finally, some successful examples of heterogenization of organocatalysts are also discussed, in the view of a potential industrial exploitation.
Highlights
Asymmetric synthesis: the query and the offerThe observation of symmetry and asymmetry in bodies and, in general, in the whole universe is an ancient matter
Chiral Brønsted acids (BAs) catalysis has had a breakthrough in asymmetric organocatalysis in 2004, when Terada and Akiyama independently presented an enantioselective Mannich-type reaction catalyzed by new metal-free phosphoric acid, BINOL-derived compounds, such as 61 (Figure 16a) [75, 76]
CONCLUDING REMARKS What lies ahead? From the number of publications, it is possible to affirm that organocatalysis is not experiencing a slowdown, presumably because many scientists have realized that its peculiarities and benefits can be exploited further and even enhanced
Summary
The observation of symmetry and asymmetry in bodies and, in general, in the whole universe is an ancient matter. A tragic example is thalidomide, a sedative drug which was broadly prescribed to pregnant women since it did not cause dependence (Figure 1b): one of the two enantiomers was responsible for foetus deformities as teratogen agent [5]. In this particular case, an additional problem is the in vivo racemization of (R)-thalidomide into the (S)-thalidomide. A more recently developed approach to asymmetric catalysis, based on organic molecules, overcomes some of the issues related to metal-based catalysts and some difficulties connected to the use of enzymes
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