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Pure Appl. Chem. Vol. 74, No. 8, pp. 1317-1325 (2002)

Pure and Applied Chemistry

Vol. 74, Issue 8

Fischer carbene complexes. A new tool for heterocyclic synthesis*

José Barluenga

Instituto Universitario de Química Organometálica "Enrique Moles", Universidad de Oviedo, 33071 Oviedo, Spain

Abstract: This short review covers our contribution in the field of the application of group 6 Fischer carbene complexes toward the synthesis of heterocyclic compounds. Alkenyl and alkynyl carbene complexes are suitable partners in [2+2], [3+2], [4+2], and [4+3] cycloaddition reactions. Moreover, chiral alkenyl carbene complexes react in sequential processes involving an initial Michael addition of a ketone lithium enolate to afford lactones with up to five consecutive stereogenic centers. Based on this strategy, we have devised a new method for the enantioselective synthesis of eight-membered carbocycles.

* Plenary lecture presented at the 3rd Florida Conference on Heterocyclic Chemistry (FloHet-III), Gainesville, Florida, USA, 6-8 March 2002. Other lectures are published in this issue, pp. 1317–1368.

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