Oxazolidinones and Related Heterocycles as Chiral Auxiliaries/Evans and Post-Evans Auxiliaries

Ligand-free Ullmann-type arylation of oxazolidinones by diaryliodonium salts

“…Among the other azaheterocycles, oxazolidinones occupy a special position due to their widespread usage in medicinal chemistry and organic synthesis. 29–32 Evans-type oxazolidinones ( N -acyloxazolidinones) are used as chiral auxiliaries in many organic transformations. 32 In addition, the approved antibiotics linezolid and tedizolid contain N -arylated oxazolidinones and are used, among other applications, in the treatment of skin infections (Fig.…”

“…29–32 Evans-type oxazolidinones ( N -acyloxazolidinones) are used as chiral auxiliaries in many organic transformations. 32 In addition, the approved antibiotics linezolid and tedizolid contain N -arylated oxazolidinones and are used, among other applications, in the treatment of skin infections (Fig. 1).…”

Chiral Bifunctional Phosphine Ligand Enables Asymmetric Trapping of Catalytic Vinyl Gold Carbene Species

“…The presence of an oxazolidinone moiety 14 in the reaction can be scope-limiting, despite its demonstrated synthetic utility as an auxiliary. Since the reaction most likely traverses through a alkenyl/acyl gold carbene intermediate, alternative access to the same type of reactive intermediates would potentially broaden the reaction scope.…”

Tandem electrocatalytic aziridination – ring expansion of simple aromatic olefins using ammonia and carbon dioxide

“…26,41,42 In addition, only a limited number of reports are successful in directly synthesizing N-unsubstituted 2-oxazolidinones. 35,43 Having N-H 2-oxazolidinones is desired for their use as a chiral auxiliary [9][10][11][12][13][14][15] and additionally offers the possibility to functionalize the nitrogen atom as required in downstream syntheses, for instance by performing the well-known Buchwald-Hartwig amination, 44,45 even immediately towards active pharmaceutical ingredients. 46,47 By replacing CO 2 with its sulfur analogue CS 2 , it is possible to synthesize 2-thiazolidinethiones 19,41,[48][49][50][51][52][53] (Scheme 1a) which possess analogous properties and applications as 2-oxazolidinones regarding both biological activity 9,[54][55][56] and organic synthetic use.…”

“…For example, linezolid (Zyvox®) and tedizolid (Sivextro®) among others are marketed worldwide for their unique antibacterial activity, even towards multidrug-resistant bacteria. [1][2][3][4][5] Additionally, 2-oxazolidinones are used as intermediates in organic synthesis, [6][7][8] as chiral auxiliaries [9][10][11][12][13][14][15] and in polymers. [16][17][18] Depending on the starting substrate, intermolecular synthetic routes for these cyclic urethanes may lead through aziridines, [19][20][21][22][23][24][25] propargylamines [26][27][28][29][30][31] or aminoalcohols [32][33][34][35][36][37] (Scheme 1a).…”