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Asymetryczna reakcja aldolowa : część I - nowe koncepcje, katalizatory i ich praktyczne zastosowanie w syntezie produktów naturalnych

Stodulski M., Młynarski J.

Wiadomości Chemiczne

2010

[Z] 64, 5-6

435-465

The aldol reaction is one of the most important method for the stereoselective construction of polyketide natural products in both – living organisms and laboratory. The tremendous development in this field has led to development of many new variants of the aldol addition. There has been some success in the use of asymmetric catalysts, although they normally rely on a Mukaiyama-type process. This reaction required a conversion of a donor substrate into more reactive species such as enol silyl ether using not less than stoichiometric amounts of a silicon reagent and a base. From atom economic perspectives, such stoichiometric amounts of reagents should be excluded from the procedures. An exciting challenge in enhancement of the efficiency of the aldol reaction is to find a compound that will catalyze direct aldol addition without pre-formation of a nucleophile and to do so asymmetrically. Direct asymmetric aldol reaction, catalyzed by both metallic complexes and purely organic molecules now becomes one of the most desired tools in organic chemistry. After an initial period of validating methodology by using a wide range of important model reactions, the time has now been reached to address specific synthesis and solve pending problems of practical relevance. In this review we describe recently discovered, most important and most flexible catalysts for direct asymmetric aldol reaction and their application in total synthesis of target natural products and known compounds of biological and pharmaceutical relevance.