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Efficient Silver‐Catalyzed Regio‐ and Stereospecific Aziridination of Dienes
Author(s) -
Llaveria Josep,
Beltrán Álvaro,
DíazRequejo M. Mar,
Matheu M. Isabel,
Castillón Sergio,
Pérez Pedro J.
Publication year - 2010
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.201003167
Subject(s) - nitrene , stereospecificity , catalysis , chemistry , stoichiometry , combinatorial chemistry , organic chemistry
Nitrene transfer : Unsymmetric dienes bearing a terminal hydroxy group can be regio‐ and stereospecifically converted into vinylaziridines upon nitrene transfer from PhINTs using a silver‐based catalyst. Stoichiometric mixtures of dienes and PhINTs were employed at low catalyst loadings (0.5 %; see scheme). The method has been applied to the synthesis of (±)‐sphingosine and gave good yields in a three‐step procedure. Ts=4‐toluenesulfonyl.