The stereoselective synthesis of vicinal amino alcohols derivatives from 1-substituted cyclopropanols and chiral --butanesulfinyl imines is described. Cyclopropanols are easily prepared from carboxylic esters upon reaction with ethylmagnesium bromide in the presence of titanium tetraisopropoxide and undergo carbon-carbon bond cleavage by means of diethylzinc to produce, upon base deprotonation, enolized zinc homoenolates, which react with chiral sulfinyl imines in a highly regio- and stereoselective manner.
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| http://dx.doi.org/10.1021/acs.joc.4c00198 | DOI Listing |
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