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

2018/03/30 by Rubén O. Torres‐Ochoa, Thomas Buyck, Qian Wang +1 · 1 citation
Chemistry · #Cyclization and Aryne Chemistry #Chemical synthesis and alkaloids #Catalytic Alkyne Reactions

paper · doi:10.1002/anie.201800746

openalex publication_date 2018/03/30 · openalex created_date 2025/10/10 · openalex updated_date 2026/07/02

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.

Cited by

• Zhu Jieping [wikipedia]

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