1. Synthesis of Vicinal anti-Amino Alcohols from N-tert-Butanesulfinyl Aldimines and Cyclopropanols
- Author
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Universidad de Alicante. Departamento de Química Orgánica, Universidad de Alicante. Instituto Universitario de Síntesis Orgánica, Hernández-Ibáñez, Sandra, Ortuño, Juan F., Sirvent, Ana, Nájera, Carmen, Sansano, Jose M., Yus, Miguel, Foubelo, Francisco, Universidad de Alicante. Departamento de Química Orgánica, Universidad de Alicante. Instituto Universitario de Síntesis Orgánica, Hernández-Ibáñez, Sandra, Ortuño, Juan F., Sirvent, Ana, Nájera, Carmen, Sansano, Jose M., Yus, Miguel, and Foubelo, Francisco
- 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.
- Published
- 2024