141902-40-1Relevant academic research and scientific papers
Acyclic stereocontrol in additions of Grignard reagents to α-alkoxyiminium ions. A stereoselective approach to threo amino ethers
Nagai,Gaudino,Wilcox
, p. 163 - 168 (1992)
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.
