Efficient Silver‐Catalyzed Regio‐ and Stereospecific Aziridination of Dienes | Zendy

Llaveria Josep | Zendy; Beltrán Álvaro | Zendy; DíazRequejo M. Mar | Zendy; Matheu M. Isabel | Zendy; Castillón Sergio | Zendy; Pérez Pedro J. | Zendy

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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.

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