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Katalizowane cynkiem asymetryczne hydrosililowanie ketonów i imin

Gajewy J.

Wiadomości Chemiczne

2013

[Z] 67, 5-6

521--562

One of the fundamental research goals in modern chemistry is the development of efficient and selective procedures to access organic compounds. Among all of the methodologies developed so far, catalysis offers an efficient and economical approach to enantiomericaly pure substances. In particular, transition metal catalysts modified by ligands, usually phosphines, are one of most successful examples of practical catalysis. Unfortunately, most of the applied metals (e.g., Pd, Rh, Ru, Ir) are low abundant, toxic and expensive. For this reason, recent research is focusing on their replacement by cheaper and low toxic metals. For example, the use of zinc can be of great interest, due to its abundance (0.0076% in the earth crust), biological relevance and distinct abilities. In the last two decades many scientific group have been working on finding new, high efficient and inexpensive catalytic system based on zinc for enantioselective transformations. It has been found that many of important organic reactions (for example aldol, Diels-Alder, Friedel-Crafts, Henry reactions) in their asymmetric version can be catalyzed by zinc complexes. One of them is also asymmetric reduction of double carbon-heteroatom bonds through addition of hydride (from silane). Hydrosilylation reduction is a promising alternative for the catalytic transformation of organic molecules to other reduction methods such as: hydrogenation and transfer hydrogenation owing to its operational simplicity and mild conditions. This review will give a general overview of the possible applications of zinc-catalyzed hydrosilylation of carbonyl compounds and imines. Since the understanding of mechanism of reaction is crucial for rational planning of new and more efficient ligands, some part of this article was devoted for mechanical considerations.