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Oxazolidinones are useful as Evans auxiliaries, which are of interest for chiral synthesis. In a common implementation, an acid chloride substrate reacts with a chiral oxazolidinone to form an imide. Substituents at the 4 and 5 position of the oxazolidinone direct any aldol reaction to the alpha position of the carbonyl of the substrate. [6]
2-Oxazolidinone is the parent compound of several protein synthesis inhibitor antibiotics and the Evans chiral auxiliaries for aldol reactions. Cycloserine is an antibiotic based on the 3-isoxazolidone parent.
Chiral auxiliaries are incorporated into synthetic routes to control the absolute configuration of stereogenic centers. David A. Evans' synthesis of the macrolide cytovaricin, considered a classic, utilizes oxazolidinone chiral auxiliaries for one asymmetric alkylation reaction and four asymmetric aldol reactions, setting the absolute stereochemistry of nine stereocenters.
Oxazolidine is a five-membered heterocycle ringwith the formula (CH 2) 3 (NH)O.The O atom and NH groups are not mutually bonded, in contrast to isoxazolidine. [2] [3] Oxazolidines (emphasis on plural) are derivatives of the parent oxazolidine owing to the presence of substituents on carbon and/or nitrogen. Oxazolines are unsaturated analogues ...
R)-2-Methylpent-4-enoic acid can be synthesized using a chiral auxiliary such an oxazolidinone derivative, popularized by David Evans. One route of synthesis consists of three steps: acylation of the oxazolidinone using triethylamine as a base, and DMAP as an acyl carrier catalyst
2‑oxazoline, 3‑oxazoline, and 4‑oxazoline (from left to right) Three structural isomers of oxazoline are possible depending on the location of the double bond, however only 2‑oxazolines are common. 4‑Oxazolines are formed as intermediates during the production of certain azomethine ylides [2] but are otherwise rare. 3‑Oxazolines are even less common but have been synthesised ...
This category has the following 2 subcategories, out of 2 total. O. Oxazolidinone antibiotics (9 P) 2-Oxazolidinones (13 P) ... 2-Oxazolidinone; P. Pemoline; S ...
A synthesis of n-aryloxazolidinones starting with an O-silyl protected ethyl(2,3-dihydroxypropyl)-carbamate was published in 2016. In a one-pot reaction the carbamate cyclisizes to a 2-oxazolidone ring under slightly basic conditions while simultaneously the oxazolidone nitrogen is arylized by copper-catalization.