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A Flexible and Stereoselective Synthesis of Azetidin‐3‐ones through Gold‐Catalyzed Intermolecular Oxidation of Alkynes
Author(s) -
Ye Longwu,
He Weimin,
Zhang Liming
Publication year - 2011
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.201007624
Subject(s) - stereoselectivity , intermolecular force , scheme (mathematics) , ring (chemistry) , combinatorial chemistry , catalysis , chemistry , computer science , organic chemistry , molecule , mathematics , mathematical analysis
Chiral rings made easy : Chiral azetidin‐3‐ones have been easily prepared from chiral N ‐propargylsulfonamides, which in turn are readily accessible through chiral sulfinamide chemistry (see scheme). Using tert ‐butylsulfonyl as the protecting group avoids unnecessary deprotection and reprotection steps, and allows its removal from the azetidine ring under acidic conditions.