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Hydration and Intramolecular Cyclization of Homopropargyl Sulfonamide Derivatives Catalyzed by Silver Hexafluoroantimonate(V): Synthesis of Structurally Diverse 2,3‐Dihydro‐1 H ‐Pyrroles
Author(s) -
Yu Xiuling,
Guo Zhonglin,
Song Hongjian,
Liu Yuxiu,
Wang Qingmin
Publication year - 2018
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201701121
Subject(s) - chemistry , intramolecular force , sulfonamide , catalysis , combinatorial chemistry , nitrogen atom , medicinal chemistry , stereochemistry , organic chemistry , ring (chemistry)
We have developed an efficient, simple protocol for synthesis of structurally diverse functionalized 2,3‐dihydro‐1 H ‐pyrroles by hydration and intramolecular cyclization of homopropargyl sulfonamide derivatives. Mechanistic experiments revealed that the sulfonamide nitrogen participated in the hydration reaction by chelating the Ag atom of the catalyst to assist in the formation of the hydration intermediate. The protocol accommodated a wide range of substrates and was used for a formal synthesis of ( S )‐nicotine.