TIETZE Domino Reaction

L. F. Tietze, Domino-reactions The tandem-Knoevenagel-hetero-Diels- Alder reaction and its application in natural product synthesis, J Heterocyclic Chem. 27 47 (1990). 

Domino reactions, in which a series of carefully planned reactions occurs in a single vessel, used to prepare complex biologically active organic compounds (Hall, 1994 Tietze, 1995). 

Tietze, L. F. (1995). Domino Reactions in Organic Synthesis. Chemistry dl Industry (19 June), 453-57. 

Tietze LF, Haunert F (2000) Domino reactions in organic synthesis. An approach to efficiency, elegance, ecological benefit, economic advantage and preservation of our resources in chemical transformations. In Vogtle F, Stoddart JF, Shibasaki M (eds) Stimulating concepts in chemistry. Wiley-VCH, Weinheim, p 39... 

Tietze L. F., Modi A. Multicomponent Domino Reactions for the Synthesis of Biologically Active Natural Products and Drugs Med. Res. Rev. 2000 20 304-322 Keywords Diels-Alder reactions... 

Tietze L. F. Domino-Reactions the Tandem-Knoevenagel-Hetero-Diels-Alder Reaction and Its Application in Natural Product Synthesis J. Heterocycl. Chem. 1990 27 47-69... 

Tietze, L.R Rackelmann, N. (2004) Domino Reactions in the Synthesis of Heterocyclic Natural Products and Analogs. Pure and Applied Chemistry, 76, 1967-1983. 

Tietze, L.F. Lieb, M.E. (1998) Domino Reactions for Library Synthesis of Small Molecules in Combinatorial Chemistry. Current Opinion in Chemical Biology, 2, 363-371. 

Tietze, L.F., Brasche, G. and Gericke, K.M. (2006) Domino Reactions in Organic Synthesis, Wiley-VCH Verlag GmbH, Weinheim. 

Domino Reactions in Organic Synthesis. Lutz F. Tietze, Gordon Brasche, and Kersten M. Gericke Copyright 2006 WILEY-VCH Verlag GmbH Co. KGaA, Weinheim ISBN 3-527 29060-5... 

One of the first enantioselective transition metal-catalyzed domino reactions in natural product synthesis leading to vitamin E (0-23) was developed by Tietze and coworkers (Scheme 0.7) [18]. This transformation is based on a Pdn-catalyzed addition of a phenolic hydroxyl group to a C-C-double bond in 0-20 in the presence of the chiral ligand 0-24, followed by an intermolecular addition of the formed Pd-spe-cies to another double bond. 

L. F. Tietze, F. Haunert, Domino Reactions in Organic Synthesis. An Approach to Efficiency, Elegance, Ecological Benefit, Economic Advantage and Preservation of our Resources in Chemical Transformations, in M. Shibasaki, J. F. Stoddart and F. Vogtle (Eds.), Stimulating Concepts in Chemistry, Wiley-VCH, Weinheim, 2000, pp. 39-64 (d) L. F. Tietze, A. Modi, Med. Res. Rev. 2000, 20, 304-322 (e) L. F. Tietze, M. E. Iieb, Curr. Opin. Chem. Biol. 

In transition metal-catalyzed domino reactions, more than one catalyst is often employed. In Tietze s definition and the classification of domino reactions, no distinction has been made between transformations where only one or more transition metal catalyst is used for the different steps, provided that they take place in a chronologically distinct order. Poli and coworkers [13] differentiated between these processes by calling them pure-domino reactions (which consisted of a single catalytic cycle driven by a single catalytic system) or pseudo-domino reactions . The latter type was subdivided into ... 

Today, multi-parallel synthesis lies at the forefront of organic and medicinal chemistry, and plays a major role in lead discovery and lead optimization programs in the pharmaceutical industry. The first solid-phase domino reactions were developed by Tietze and coworkers [6] using a domino Knoevenagel/hetero-Diels-Alder and a domino Knoevenagel/ene protocol. Reaction of solid-phase bound 1,3-dicarbonyl compounds such as 10-22 with aldehydes and enol ethers in the presence of piperidinium acetate led to the 1-oxa-1,3-butadiene 10-23, which underwent an intermolecular hetero-Diels-Alder reaction with the enol ethers to give the resin-bound products 10-24. Solvolysis with NaOMe afforded the desired dihydro-pyranes, 10-25 with over 90 % purity. Ene reactions have also been performed in a similar manner [7]. 

Tietze LF, Brasche G, Gericke KM (2006) Domino reactions in organic synthesis. Wiley-VCH, Weinheim... 

Multicomponent reactions of this type, in the concepts of Tietze, who introduced the term domino reactions (96CRV115), can also be regarded as domino reactions of the type Knoevenagel-Michael-ljef-ero-Thorpe-Ziegler in accordance with the probable mechanistic scheme (Scheme 32). 

For the concept of domino reactions in organic synthesis see a) L. F. Tietze,... 

Efficient and elegant syntheses of complex organic molecules with multiple stereogenic centers continue to be important in both academic and industrial laboratories (Nicolaou et al. 2003, 2006). In particular, catalytic asymmetric multicomponent domino reactions, used in the course total syntheses of natural products and synthetic building blocks, are highly desirable (Nicolaou et al. 2003, 2006 Tietze and Beifuss 1993 Tietze 1996 Tietze and Haunert 2000 Wasilke et al. 2005 Ramon and Yus 2005 Guo and Ma 2006 Pellissier 2006 Pellisier 2006 Tietze... 

Tietze LF (1996) Domino reactions inorganic synthesis. Chem Rev 96 115-136... 

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