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Practical Synthesis of β‐Ketothioesters by Acid‐Catalyzed Hydrolysis of Ketene N,S ‐Acetals with Amino as the Leaving Group
Author(s) -
Xu Qi,
Zheng Baihui,
Pan Ling,
Liu Qun,
Li Yifei
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201900634
Subject(s) - ketene , chemistry , nucleophile , hydrolysis , catalysis , acetal , acid hydrolysis , leaving group , organic chemistry , functional group , medicinal chemistry , combinatorial chemistry , polymer
A Novel, general, and highly efficient methodology for the synthesis of β‐ketothioesters from ketene N,S ‐acetals has been developed. In this acid‐catalyzed reaction, the amino group, including both alkylamino and arylamino groups, of α‐oxo ketene N,S ‐acetals can be easily displaced in the presence of H 2 O as nucleophile (hydrolysis) instead of the alkylthiol group reported. This new method is simple and practical. A series of β‐ketothioesters were prepared in high yields with broad tolerance of substrates under mild reaction conditions.