Convenient Synthesis of Oxazolidinones and Oxazinones from Allyl and Homoallyl Amines under Mild Conditions

Antibiotics from Carbon Dioxide: Sustainable Pathways to Pharmaceutically Relevant Cyclic Carbamates

“…Cyclization of allylic amines and CO 2 to give 5‐substituted oxazolidinones is carried out in tandem with in situ double bond functionalization, such as fluoroalkylation or iodination (Schemeà). While this places some restrictions on the substrate scope, it can also be seen as an advantage, as more complex structures can be accessed in few steps.…”

“…Iodination methods also allow for the assembly of fused rings via double cyclization, if the amine is primary and the double bond is more than three carbons removed from the nitrogen. [62c]…”

“…Cyclization of carbon dioxide and allylic amines in tandem with (a) iodination[62a] or (b) fluoroalkylation[61b], [61c] of the double bond.…”

In situ tether formation from amines and alcohols enabling highly selective Tsuji–Trost allylation and olefin functionalization

“…For a long time, difunctionalization of olefins via in situ tether formation has been limited to oxy- or amino-halogenation reactions using carbon dioxide. 9 The obtained products are highly attractive for further functionalization and research in this area is therefore still ongoing. A highly efficient method for the oxy- and amino-iodation of both allylic alcohols and amines was developed by Minakata and co-workers using tert -butyl hypoiodite as iodine source with only one atmosphere of carbon dioxide.…”

“… 8 The use of carbon dioxide as tether precursor is even more challenging, and most success have been met for oxyhalogenation reactions. 9 A disadvantage of the use of carbonyls as tethers is that cleavage can require relatively harsh reaction conditions. In this case, sp 3 hybridized carbon tethers could be considered, as the obtained acetals, hemiaminals or aminals can be cleaved under milder conditions.…”