27557-41-1Relevant academic research and scientific papers
Desamination of β- and γ-Amino Alcohols
Guenther, Bernd-Rainer,Kirmse, Wolfgang
, p. 518 - 532 (2007/10/02)
Nitrous acid deaminations of the β-amino alcohols 2 and 12 afford 1,2 diols as well as ketones by pinacolic rearrangement.Both types of products arise with predominant inversion of configuration.Stereochemical studies and isotopic labeling reveal that formation of the diols involves an oxygen shift, presumably via oxirane intermediates.Deamination of the γ-amino alcohol 37 induces, in part, sequential rearrangements to give products also obtained from 12, but in different proportions and enantiomeric purities.Conformational control provides a reasonable explanation of our results.
