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Pure Appl. Chem., 2002, Vol. 74, No. 1, pp. 175-180

Stereoselective syntheses of heterocycles via metallated alkoxyallenes

Hans-Ulrich Reissig, Wolfgang Schade, G. Marlyse Okala Amombo, Robert Pulz and Arndt Hausherr

Institut für Chemie ­ Organische Chemie, Freie Universität Berlin, Takustr. 3, D-14195 Berlin, Germany

Abstract: n-Butyllithium smoothly deprotonates alkoxyallenes at C-1. The generated lithiated species reacts with a variety of electrophiles furnishing after cyclization functionalized furan, pyrrole, or 1,2-oxazine derivatives. The formation of new C­C bonds often occurs with high stereoselectivities, which are exploited for efficient and selective syntheses of natural products or other compounds of interest.