title: Alkoxyallenes as building blocks for organic synthesis.
abstract: Alkoxyallenes are unusually versatile C3 building blocks in organic synthesis. Hence this tutorial review summarizes the most important transformations, including subsequent reactions and their applications in the synthesis of relevant compounds, e.g. natural products. The reactivity patterns involved and the synthons derived from alkoxyallenes are presented. Often alkoxyallenes can serve as substitutes of acrolein or acrolein acetals, utilisation of which has already led to interesting products. Most important is the use of lithiated alkoxyallenes which smoothly react with a variety of electrophiles and lead to products with unique substitution patterns. The heterocycles or carbocycles formed are intermediates for the stereoselective synthesis of natural products or for the preparation of other structurally relevant compounds. The different synthons being put into practice by the use of lithiated alkoxyallenes in these variations will be discussed.
authors.affiliation: Institut für Chemie und Biochemie, Freie Universität Berlin, Takustrasse 3, 14195 Berlin, Germany. hans.reissig@chemie.fu-berlin.de.
authors.forename: Reinhold
authors.initials: R
authors.lastname: Zimmer
authors.forename: Hans-Ulrich
authors.initials: HU
authors.lastname: Reissig
mesh_terms: D000438:Alcohols / Q000138:chemical synthesis / Q000737:chemistry*; D000466:Alkadienes / Q000138:chemical synthesis / Q000737:chemistry*; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D060326:Chemistry Techniques, Synthetic / Q000379:methods*; D061565:Cycloaddition Reaction / Q000379:methods; D006571:Heterocyclic Compounds / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000438:Alcohols; D000466:Alkadienes; D001688:Biological Products; D006571:Heterocyclic Compounds; C059688:alkoxyl radical; C025947:propadiene