Oxazolidin-2-one Ring, a Popular Framework in Synthetic Organic Chemistry Part 2 [1]. Applications and Modifications

Abstract

The present review is mainly focused upon the use of C-substituted oxazolidin-2-ones as chiral auxiliaries in the stereocontrolled C-C and C-X (X = hetero atom) bond formation.The recent progress in the stereoselective alkylation, cycloaddition and aldol reaction, as well as in the 1,4-coniugate addition, in [2+2]photocycloaddition, in Lewis acid promoted free-radical copolymerization reactions are discussed. Emerging new applications of the oxazolidin-2-one nucleus, such as building blocks in the design and preparation of foldamers or as organocatalyst in enantioselective epoxidation reactions, will be also discussed.

Synthesis of Constrained Peptidomimetics Containing 2‐Oxo‐1,3‐oxazolidine‐4‐carboxylic Acids

“…1 H NMR spectra were recorded at 400 MHz at room temperature in CDCl 3 /[D 6 ]DMSO (2:1) by using 5 mm tubes; 13 C NMR spectra were recorded at 75 MHz. Chemical shifts are reported as δ values relative to the CDCl 3 signal.…”

“…is well documented. [13] However, this work describes a new, highly efficient synthesis of some representative examples of Oxd-peptides directly from a peptide sequence, either in solution or in the solid phase. Furthermore, to demonstrate the utility of the procedure in medicinal chemistry, a constrained analogue of the endogenous opioid peptide endomorphin-1 (EM1), [14] H-TyrPro-Trp-PheNH 2 , with the 2-oxo-oxazolidine-4-carboxylate in position 2 was prepared as a proline mimetic; the compound was characterized by a trans conformation of the preceding peptide bond.…”

Synthesis of (±)‐trans‐hexahydropyrrolo[3,4‐d]oxazol‐2‐one and its derivatives by using N‐(tert‐butyloxycarbonyl)‐3‐pyrroline as precursor

“…On the other hand, 4b on protection with Boc 2 O gives the di-tert-boc protected compound which on further treatment with mesyl chloride, tosyl chloride, or thionyl chloride, the corresponding fused 2-oxazolidinone was not achieved [14]. Thus, we have studied the scope of this approach by opening of epoxy compound 8 with different amines.…”

Synthesis of Oxazolidin‐2‐ones via a Copper(I)‐Catalyzed Tandem Decarboxylative/Carboxylative Cyclization of a Propiolic Acid, a Primary Amine and an Aldehyde

“…In the past decades, a variety of protocols has been reported for the syntheses of oxazolidin-2-ones including the cyclization of carbonyl compounds with aamino acids or 1,2-amino alcohols, [3] the [2 + 3] coupling between heterocumulenes and oxiranes or aziridines, [4] cyclocarbamations [5] and Au-catalyzed cyclization of N-Boc-propargylic amines. [6] The cycloaddition procedure of propargylic amines with CO 2 is a very attractive alternative as CO 2 is an easily available, renewable and environmentally benign substrate.…”