DOI: 10.1021/acs.joc.6c02045 ISSN: 0022-3263
Enantioselective Amination of In Situ Generated Alkyl Gold Species with Azocarboxamide as the N -Source
Yufei Zhang, Ming Bao, Xinfang XuAbstract
Herein, we report an enantioselective electrophilic amination reaction of alkylgold species, generated in situ from N-propargylamides, using azocarboxamides as the N-source. This transformation is realized through synergistic catalysis by a combination of a gold complex and a chiral quinine-derived squaramide (QN-SQA), yielding chiral alkylideneoxazolines incorporating a nitrogen-containing tertiary carbon stereocenter with good to high yields and excellent enantioselectivities. Furthermore, the synthetic utility of these products is demonstrated through their versatile transformations, providing a complementary method for constructing poly-substituted and fused oxazole derivatives.