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Synthesis 1992; 1992(1/2): 163-168
DOI: 10.1055/s-1992-34180
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Acyclic Stereocontrol in Additions of Grignard Reagents to α-Alkoxyiminium Ions. A Stereoselective Approach to threo Amino Ethers

Mitsuo Nagai* , John J. Gaudino, Craig S. Wilcox
  • *Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA
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Publication Date:
18 September 2002 (online)

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The data in this paper suggest that reactions of Grignard reagents with dialkylaminofuranosides derived from pentoses proceed via α-alkoxyiminium ions and that these α-alkoxyiminium ions react quite stereoselectively. The rate of this reaction is dependent on the substituent at the 5-position of the pentose. A 5-deoxy analog is shown to react very slowly compared with a 5-O-methoxymethyl derivative. Importantly, the face selectivity of iminium ions with nucleophiles is shown to be opposite that expected and observed for reactions of aldehydes. A predictive mechanistic model is presented.