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.
*Lecture presented at the 11th IUPAC International
Symposium on Organometallic Chemistry Directed Towards Organic Synthesis
(OMCOS-11), Taipei, Taiwan, 22-26 July 2001. Other presentations are
presented in this issue, pp.1-186.
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