2Oxazolidinone

2-Oxazolidinone is a five-membered heterocyclic organic compound containing both nitrogen and oxygen atoms within its ring structure. Its chemical formula is C3H5NO2. The molecule features a carbonyl group (C=O) adjacent to the nitrogen atom, forming an amide linkage, and an oxygen atom attached to the carbon adjacent to the nitrogen. This cyclic structure is planar.

In organic synthesis, 2-oxazolidinone and its derivatives are important building blocks and chiral auxiliaries. Chiral auxiliaries are groups that can be temporarily attached to a molecule to control the stereochemistry of a reaction. After the desired stereochemical outcome is achieved, the auxiliary can be removed. The rigid structure of the oxazolidinone ring can effectively direct incoming reagents to one face of a molecule, leading to highly enantioselective transformations.

A prominent application of 2-oxazolidinone derivatives is in asymmetric synthesis, particularly in reactions like alkylations, aldol additions, and Diels-Alder reactions. For instance, Evans' oxazolidinones, developed by David A. Evans, are widely used chiral auxiliaries that have enabled the efficient synthesis of complex chiral molecules, including pharmaceuticals and natural products. The ease of their attachment, their effectiveness in controlling stereochemistry, and their relatively straightforward removal make them valuable tools in modern organic chemistry.