Oxazolidinone represents a class of most important five‐membered cyclic carbamates. They are of great significance for modern organic synthesis and are widespread as pharmacologically active compounds. This review summarizes recent advances in the chemistry of 2‐oxazolidinones, with an emphasis on their synthesis, employing different catalytic systems or catalyst‐free conditions, as well as on their ring‐opening transformations through decarboxylative coupling, covering the period from 2010 to early 2021. Detailed mechanistic aspects are highlighted, hoping to help researchers to explore the hidden opportunities for reaction discoveries.

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An efficient and selective method for metal- and oxidant-free deaminated esterification of tertiary amines is presented. In this protocol, ynoates play a key role to activate the Csp3−N bond through a process of in situ generation of zwitterionic salts. The transformations show that Csp3−N bond in the zwitterionic species has a lower dissociation energy than Csp2−N bond, leading to break preferentially and be trapped by carboxylic acids to generate the corresponding products in moderate to good yield.

We present an economical and facile catalytic reduction process of carboxylic acids for the synthesis of alcohols. This pyridine‐catalyzed strategy operates through addition of carboxylic acids with methyl propiolate followed by NaBH4 reduction or unexpected ester exchange, providing the corresponding primary alcohols and esters, respectively. A range of carboxylic acids bearing other reductive groups (e. g., halogen, cyano, nitro, ester and double bond) are accessed with uniformly high chemoselectivity. The use of environmentally benign, convenient and safe procedure also makes this catalytic protocol attractive for practical application.