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Ruthenium‐Catalyzed Oxidative Transformations of Terminal Alkynes to Ketenes By Using Tethered Sulfoxides: Access to β‐Lactams and Cyclobutanones
Author(s) -
Wang Youliang,
Zheng Zhitong,
Zhang Liming
Publication year - 2014
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.201403796
Subject(s) - cycloaddition , chemistry , catalysis , ketene , ruthenium , oxidative phosphorylation , bicyclic molecule , terminal (telecommunication) , medicinal chemistry , combinatorial chemistry , organic chemistry , computer science , telecommunications , biochemistry
The oxidation of in situ generated Ru vinylidenes to ketenes is realized with tethered sulfoxides. The result is a Ru‐catalyzed oxidative transformation of terminal alkynes to highly valuable ketenes. Moreover, the ketenes generated here were shown to undergo characteristic ketene [2+2] cycloaddition reactions with tethered alkenes and external imines, yielding synthetically versatile bicyclic cyclobutanones and β‐lactams, respectively.