Five-Membered Cyclic Phosphorylating Reagents and Related Compounds

Abstract

The conceptual and mechanistic basis, as well as a selection of typical results for five-membered cyclic phosphorylating reagents and related compounds are briefly discussed. The historical development from Westheimer's experiment to the so-called programmed phosphorylating reagents for the synthesis of naturally occurring phosphorylated compounds and the modern reagents and techniques for the synthesis of phospholipids, and also cyclic chiral derivatizing agents (CDA) are presented. 1. Introduction 2. The Westheimer Experiment 3. CAP- and CEP-Derivatives as Phosphorylating Reagents 4. Programmed Phosphorylating Reagents 5. Syntheses of Phospholipids via Cyclic Phosphorylating Reagents 5.1. Synthesis of Phospholipids via Cyclic Enediol Phosphates 5.2. Particular Advantages of Cyclic Reagents 5.2.1. Synthesis of Phosphatidyl Choline Derivatives via Dioxa-phospholanes 5.2.2. Synthesis of Phospholipids via Oxazaphospholidines 6. Miscellaneous 7. Conclusion