Alkoxyallenes as building blocks for organic synthesis

• Published in: Chemical Society reviews Vol. 43; no. 9; pp. 2888 - 2903
• Main Authors: Zimmer, Reinhold, Reissig, Hans-Ulrich
• Format: Journal Article
• Language: English
• Published: England 07.05.2014
• Subjects: Acetals; Acroleins; Alcohols - chemical synthesis; Alcohols - chemistry; Alkadienes - chemical synthesis; Alkadienes - chemistry; Biological Products - chemical synthesis; Biological Products - chemistry; Chemistry Techniques, Synthetic - methods; Cycloaddition Reaction - methods; Heterocyclic Compounds - chemical synthesis; Heterocyclic Compounds - chemistry; Natural products; Stereoisomerism; Synthesis; Synthesis (chemistry); Transformations
• ISSN: 0306-0012; 1460-4744
• DOI: 10.1039/c3cs60429b

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.