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Rhodium(II)‐catalyzed nitrene transfer with phenyliodonium ylides
Author(s) -
Mueller Paul,
Baud Corine,
Naegeli Ivo
Publication year - 1998
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/(sici)1099-1395(199808/09)11:8/9<597::aid-poc45>3.0.co;2-m
Subject(s) - nitrene , chemistry , rhodium , catalysis , stereospecificity , medicinal chemistry , walden inversion , decomposition , stereochemistry , organic chemistry
The [Rh 2 (OAc) 4 ]‐catalyzed decomposition of NsN=IPh {[ N ‐( p ‐nitrobenzenesulfonyl)imino]phenyliodinane} affords aziridines in the presence of olefins and insertion products with compounds having activated CH bonds. The aziridination is stereospecific, and the insertion proceeds with retention of configuration. With chiral Rh(II) complexes, enantioenriched products result. A one‐step mechanism involving a metal‐complexed nitrene is proposed for both reactions. © 1998 John Wiley & Sons, Ltd.