Stereoselective syntheses of heterocycles via metallated alkoxyallenes

Author:

Reissig Hans-Ulrich1,Schade Wolfgang1,Okala Amombo G. Marlyse1,Pulz Robert1,Hausherr Arndt1

Affiliation:

1. 1Institut 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.

Publisher

Walter de Gruyter GmbH

Subject

General Chemical Engineering,General Chemistry

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