2020
DOI: 10.1007/7081_2020_36
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Oxazolidinones and Related Heterocycles as Chiral Auxiliaries/Evans and Post-Evans Auxiliaries

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Cited by 6 publications
(6 citation statements)
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“…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.…”
Section: Introductionmentioning
confidence: 99%
See 1 more Smart Citation
“…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.…”
Section: Introductionmentioning
confidence: 99%
“…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).…”
Section: Introductionmentioning
confidence: 99%
“…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.…”
mentioning
confidence: 99%
“…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.…”
mentioning
confidence: 99%
“…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).…”
mentioning
confidence: 99%