Decarboxylative ring-opening of 2-oxazolidinines: A straightforward method for the synthesis of chiral beta-chalcogen amines

Chalcogen amines (CAs) are a privileged class of compounds especially because of their ability to mimic the activity of GPx.1 Additionally, chiral chalcogen amines (CCAs) have also been successfully applied as both, chiral ligands and organocatalysts in asymmetric synthesis.2 Despite this, the preparation of CCAs remains a significant challenge in organic synthesis. Typical protocols comprise a multi-step linear synthesis, involving tedious protecting-deprotecting steps and activation of alcohols for the insertion of chalcogen moyiety.3 Besides, monoalkylation of amine group is commonly a difficult task in these methodologies. Since the preparation of CCA blocks in large amounts is a major concern in our group, we decided to investigate a decarboxylative ring-opening reaction of 2-oxazolidinones (commercially available feedstock) by chalcogen nucleophiles as a strategy to accomplish their synthesis. The established protocol, in addition to providing a much shorter synthesis for CCAs, can be easily adapted for the monoalkylation of the amine group.