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Surfactant‐Type Brønsted Acid Catalyzed Stereoselective Synthesis of trans ‐3‐Alkenyl Indazoles from Triazenylaryl Allylic Alcohols in Water
Author(s) -
Yang Weijun,
Yang Zhigen,
Xu Lijun,
Zhang Lili,
Xu Xin,
Miao Maozhong,
Ren Hongjun
Publication year - 2013
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201306632
Subject(s) - stereoselectivity , pyrrolidine , chemistry , sulfonic acid , allylic rearrangement , brønsted–lowry acid–base theory , catalysis , benzene , pulmonary surfactant , organic chemistry , medicinal chemistry , polymer chemistry , biochemistry
Testing the waters : An efficient dodecyl benzene sulfonic acid (DBSA) catalyzed approach to the synthesis of the title compounds in water is reported. Furthermore, upon cleavage of the pyrrolidine group from the trans ‐3‐alkenyl‐2‐pyrrolidine‐2 H ‐indazoles with Zn in CH 3 COOH, trans ‐3‐alkenyl‐1 H ‐indazoles are obtained in good to excellent yields.