title: A highly efficient Mukaiyama-Mannich reaction of N-Boc isatin ketimines and other active cyclic ketimines using difluoroenol silyl ethers catalyzed by Ph3PAuOTf.
abstract: Ph3PAuOTf is identified as a powerful catalyst for the addition of difluoroenol silyl ethers to N-Boc isatin ketimines and other two kinds of active cyclic ketimines. This represents the first Au(i)-catalyzed Mukaiyama-Mannich reaction, and the corresponding non-fluorinated enol silyl ether proves to be even much more reactive under the same conditions. This method paves the way to the total synthesis of difluoromethylated analogues of AG-041R, a gastrin/CCK-B receptor antagonist.
authors.affiliation: Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, 3663N, Zhongshan Road, Shanghai 200062, China. jzhou@chem.ecnu.edu.cn.
authors.forename: Jin-Sheng
authors.initials: JS
authors.lastname: Yu
authors.forename: Jian
authors.initials: J
authors.lastname: Zhou
mesh_terms: D002384:Catalysis; D003500:Cyclization; D004987:Ethers / Q000737:chemistry; D006046:Gold / Q000737:chemistry*; D054879:Halogenation; D007097:Imines / Q000737:chemistry*; D007211:Indoles / Q000737:chemistry*; D007510:Isatin / Q000737:chemistry*; D008352:Mannich Bases / Q000737:chemistry; D008745:Methylation; D009570:Nitriles / Q000737:chemistry*
chemical_list: C109755:AG-041R; D004987:Ethers; D007097:Imines; D007211:Indoles; D008352:Mannich Bases; D009570:Nitriles; C542835:ketimine; D006046:Gold; D007510:Isatin