170751-28-7Relevant academic research and scientific papers
77. Carbenoid Reactions in Rhodium(II)-Catalyzed Decomposition of Iodonium Ylides
Mueller, Paul,Fernandez, Daniel
, p. 947 - 958 (1995)
The intermediacy of metallocarbenes in decomposition reactions of iodonium ylides with was established by comparison with reactions of the corresponding diazo compounds.The sensitivity of the RhII-catalyzed intermolecular cyclopropa
The enantioselectivity and the stereochemical course of copper-catalyzed intramolecular CH insertions of phenyliodonium ylides
Mueller, Paul,Bolea, Christelle
, p. 483 - 494 (2007/10/03)
The Cu-catalyzed intramolecular CH insertion of phenyliodonium ylide 1b was investigated at 0° in the presence of several chiral ligands. Enantioselectivities varied in the range 38-72%, and were higher than those resulting from reaction of the diazo compound 1c at 65°. The intramolecular insertion of the enantiomerically pure methyl diazoacetate (R)-20 and of the corresponding phenyliodonium ylide (R)-21 proceeded to (R)-23 with retention of configuration with [Cu(hfa)2] (hfa = hexafluoroacetylacetone = 1,1,1,5,5,5-hexafluoropentane-2,4-dione) and [Rh2(OAc)4]. These results are consistent with a carbenoid mechanism for the Cu-catalyzed insertion with phenyliodonium ylides. However, the insertion of the perfluorosulfonated phenyliodonium ylide (R)-29 afforded with [Cu(hfa)2] as well as with [Rh2(OAc)4] the cyclopentanone derivative 30 as a cis/trans mixture with only 56-67% enantiomeric excess.
