A highly efficient Mukaiyama–Mannich reaction of N-Boc isatin ketimines and other active cyclic ketimines using difluoroenol silyl ethers catalyzed by Ph3PAuOTf. Issue 45 (7th October 2015)

• Record Type: Journal Article
• Authors: Yu, Jin-Sheng; Zhou, Jian
• Is Part Of: Organic & biomolecular chemistry. Volume 13:Issue 45(2015)
• Page Start: 10968
• Page End: 10972
• Publication Date: 2015-10-07
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c5ob01895a
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : A Ph3 PAuOTf catalyzed highly efficient reaction of difluoroenoxysilanes and active ketimines is reported, which represents the first Au(i )-catalyzed Mukaiyama–Mannich reaction. Abstract : Ph3 PAuOTf 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.