Stereoselective β-Hydrogen Elimination from Nickel(II)-N-Glycoside Complexes

Journal of Organic Chemistry

Volumn 62, Issue 7, 1997, Pages 2152-2154

  Smith, Glenn ^a   Pedersen, Steven F ^a   Leary, Julie A ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001150790     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9622789     Document Type: Article

References (25)

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14. LAB) used in the MS/MS experiments was 10 eV.
15. Product ion spectra of all isotopically labeled complexes are provided as Supporting Information.
16. We propose that a certain population of the m / z 293 ions exist as the alkoxide. If the aminal nitrogen was exclusively deprotonated, and ring opening/fragmentation preceded β-hydrogen elimination, then one would expect to see no difference in the intensities of the m / z 201 ion between, for example, glucose and mannose since the newly formed C-3 carbanionic intermediates would be enantiomeric.
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