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An Efficient Approach to Chiral Allyloxyamines by Stereospecific Allylation of Nitrosoarenes with Chiral Allylboronates
Author(s) -
Li Yuanming,
Chakrabarty Shyamal,
Studer Armido
Publication year - 2015
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.201410188
Subject(s) - stereospecificity , regioselectivity , chirality (physics) , allylic rearrangement , chemistry , selectivity , combinatorial chemistry , catalysis , organic chemistry , physics , chiral anomaly , quantum mechanics , fermion , nambu–jona lasinio model
A novel and efficient approach to allyloxyamines by the allylation of nitrosoarenes with α‐chiral allylboronates is described. CO bond formation occurs with high stereospecificity and the product allyloxyamines are easily transformed into valuable chiral building blocks such as isoxazolidines and allylic alcohols. The reaction features complete regioselectivity (O‐selectivity), high E/Z selectivity, and excellent chirality transfer.