Hernández-Ibáñez, Sandra, Ortuño, Juan F., Sirvent, Ana, Nájera, Carmen, Sansano, Jose M., Yus, Miguel, Foubelo, Francisco
Synthesis of Vicinal anti-Amino Alcohols from N-tert-Butanesulfinyl Aldimines and Cyclopropanols
The Journal of Organic Chemistry. 2024, 89(9): 6193-6204. https://doi.org/10.1021/acs.joc.4c00198
URI: http://hdl.handle.net/10045/142152
DOI: 10.1021/acs.joc.4c00198
ISSN: 0022-3263 (Print)
Abstract: 
The stereoselective synthesis of vicinal amino alcohols derivatives from 1-substituted cyclopropanols and chiral N-tert-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.
Keywords:Stereoselective synthesis, Vicinal amino alcohols, Cyclopropanols, N-tert-butanesulfinyl imines
American Chemical Society
info:eu-repo/semantics/article