Organocopper chemistry

Organocopper chemistry is still rapidly expanding its syntlietic scope. Hie scope of carbocupration, previously limited to acetylenes, has recently been extended to olefins [33-36]. 1,6-, 1,8-, 1,10-, and 1,12-Addition and 1,5-Su2" substitution reac-... 

Rnochel P, Betzemeier B (2002) In Krause N (ed) Modem organocopper chemistry. Wiley-VCH, Weinheim, Chapter 2... 

Krause, N., Ed. Modem Organocopper Chemistry, Wiley-VCH Weinheim, 2002. 

Feringa, B. L. Naasz, R. Imbos, R. Arnold, L. A. Copper-catalyzed Enantioselective Conjugate Addition Reactions of Organozinc Reagents. In Modem Organocopper Chemistry Krause, N. Ed. Wiley-VCH GmbH Weinheim, 2002 Chapter 7, pp 224—258. 

Organocopper chemistry also provides a straightforward synthesis through a special alkylation procedure (Scheme 7-22). An organocopper reagent, generated in situ from equimolar amounts of co-side chain vinyl lithium, Cul, and... 

Due to the distance between the stereogenic center and the place of the nucleophilic attack, the enantioselective 1,5-substitution of chiral enyne acetates constitutes one of the rare cases of remote stereocontrol in organocopper chemistry. Moreover, the method is not limited to substrate 51, but can also be applied to the synthesis of enantiomerically enriched or pure vinylallenes 53-57 with variable substituent patterns (Scheme 2.20) [28]. 

Krause, N., Hoffinann-Roder, A. In Modem Organocopper Chemistry, Krause, N. (Ed.), Wiley-VCH Weinheim, 2002, pp. 145 and references cited therein. 

Modem Organocopper Chemistry. Edited by Norbert Krause Copyright 2002 Wiley-VCH Verlag GmbH ISBNs 3-527-29773-1 (Hardcover) 3-527-60008-6 (Electronic)... 

Organocopper chemistry remains a mainstay of organic synthesis because of the range of copper-promoted transformations on offer and because it is often complementary to palladium chemistry and alkali and alkaline earth organometallic... 

The author s work in organocopper chemistry has been made possible by the generous support of the National Science Foundation (NSF), the American Chemical Society-Petroleum Research Fund (ACS-PRF) and the National Institutes of Health (NIH). Thanks and appreciation go to the graduate students and postdoctoral fellows who made the chemistry work. A special thank goes to Dr. Ross Mabon and Dr. Kishan R. Chandupatla for carefully reading the entire manuscipt. 

For a recent review on mechanistic aspects of organocopper chemistry see E. Nakamura, S. Mori, Angew. Chem. 2000, 112, 3902-3924 Angew. Chem. Int. Ed. 2000, 39, 3750-3771 and references cited therein. 

Conjugate addition [2] to Michael acceptors is the most important and useful reaction in organocopper chemistry, and the reaction is often used as the key step in the synthesis of numerous natural and unnatural products. Perhaps one of the most efficient methods for the synthesis of quaternary carbon centers is organo-copper-mediated conjugate addition to /I, yS-disubstituted enones. 

Sn2 substitution reactions of alkyl halides with hard nucleophiles such as alkyl anions can be achieved most readily with the aid of organocopper chemistry [95]. Sn2 reactions with epoxides and aziridines are also synthetically useful [96]. The... 

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