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Brønsted Acid‐Promoted Diastereoselective [4+1] Cyclization Reaction of Enamides and Sulfoxonium Ylides
Author(s) -
Luo Nan,
Zhan Zhenzhen,
Ban Zihui,
Lu Guoqiang,
He Jianping,
Hu Fangpeng,
Huang Guosheng
Publication year - 2020
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.202000567
Subject(s) - chemistry , brønsted–lowry acid–base theory , catalysis , reaction conditions , combinatorial chemistry , metal , organic chemistry , medicinal chemistry
Abstract A metal‐free synthesis of trisubstituted trans‐oxazolines using enamides and sulfoxonium ylides was developed in this study. A [4+1] cyclization reaction was realized by the formation of C−C and C−O bonds under mild conditions, wherein the reaction was catalyzed by HClO 4 . This strategy produced trans‐oxazolines in good yields with considerable diastereoselective control and is sufficient for large‐scale synthesis.