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Stereospecific Formal [3+2] Dipolar Cycloaddition of Cyclopropanes with Nitrosoarenes: An Approach to Isoxazolidines
Author(s) -
Chakrabarty Shyamal,
Chatterjee Indranil,
Wibbeling Birgit,
Daniliuc Constantin Gabriel,
Studer Armido
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.201400885
Subject(s) - cycloaddition , regioselectivity , stereospecificity , chemistry , cleavage (geology) , aryl , bond cleavage , combinatorial chemistry , catalysis , stereochemistry , organic chemistry , biology , alkyl , fracture (geology) , paleontology
The MgBr 2 ‐catalyzed formal [3+2] cycloaddition of donor–acceptor activated cyclopropanes with nitrosoarenes offers a novel approach to various structurally diverse isoxazolidines. The reactions, which are experimentally easy to conduct, occur with complete stereospecificity and perfect control of regioselectivity. Product isoxazolidines can be readily transformed into α‐amino lactones by reductive or decarboxylative NO cleavage and subsequent lactonisation, and the N‐aryl bond cleavage is also possible under oxidative conditions.