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- Title
Heteroannulation of Arynes with α‐Amino Imides: Synthesis of 2,2‐Disubstituted Indolin‐3‐ones and Application to the Enantioselective Total Synthesis of (+)‐Hinckdentine A.
- Authors
Torres‐Ochoa, Rubén O.; Buyck, Thomas; Wang, Qian; Zhu, Jieping
- Abstract
Abstract: A novel heteroannulation reaction between α‐amino imides and in situ generated arynes has been developed for the synthesis of 2,2‐disubstituted indolin‐3‐ones. An enantioselective total synthesis of the marine alkaloid (+)‐hinckdentine A was subsequently accomplished using this reaction as a key step. A catalytic enantioselective Michael addition of an α‐aryl‐α‐isocyanoacetate to phenyl vinyl selenone was employed for the construction of the enantioenriched α‐quaternary α‐amino ester.
- Subjects
INDOLINONE; ARYNE; CHEMICAL synthesis; ENANTIOSELECTIVE catalysis; MICHAEL reaction
- Publication
Angewandte Chemie, 2018, Vol 130, Issue 20, p5781
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201800746