Oxazolidin-2-one Ring, a Popular Framework in Synthetic Organic Chemistry: Part 1. The Construction of the Oxazolidin-2-one Ring

Abstract

The 1,3-oxazolidin-2-one nucleus is a popular heterocycle framework in synthetic organic chemistry, as well as in medicinal chemistry. This paper deals with the huge number of synthetic approaches addressed to the construction of this five-member ring, with a particular care for the mechanistic and stereochemical outcome. The 2-oxo-1,3-oxazolidine ring is a cyclic carbamate skeleton quite rare in natural product chemistry but very popular in the Synthetic Organic Chemistry since the Evans' report (1) in 1981 on the use of enantiomerically pure 4- substituted oxazolidin-2-ones as chiral auxiliaries in asymmetric synthesis. Oxazolidinones have also a large application as protective groups for the 1,2-aminoalcohol system. Finally, the introduction in the pharmaceutical market of Linezolid (2), an oxazolidin-2-one-based antibacterial drug, attracted the interest of the scientists and resulted in the production of several publications.