Synthesis of Vicinal anti-Amino Alcohols from N-tert-Butanesulfinyl Aldimines and Cyclopropanols
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http://hdl.handle.net/10045/142152
| Title: | Synthesis of Vicinal anti-Amino Alcohols from N-tert-Butanesulfinyl Aldimines and Cyclopropanols |
|---|---|
| Authors: | Hernández-Ibáñez, Sandra | Ortuño, Juan F. | Sirvent, Ana | Nájera, Carmen | Sansano, Jose M. | Yus, Miguel | Foubelo, Francisco |
| Research Group/s: | Síntesis Asimétrica (SINTAS) |
| Center, Department or Service: | Universidad de Alicante. Departamento de Química Orgánica | Universidad de Alicante. Instituto Universitario de Síntesis Orgánica |
| Keywords: | Stereoselective synthesis | Vicinal amino alcohols | Cyclopropanols | N-tert-butanesulfinyl imines |
| Issue Date: | 13-Apr-2024 |
| Publisher: | American Chemical Society |
| Citation: | The Journal of Organic Chemistry. 2024, 89(9): 6193-6204. https://doi.org/10.1021/acs.joc.4c00198 |
| 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. |
| Sponsor: | We acknowledge the continued financial support from the Spanish Ministerio de Economía y Competitividad (CTQ2017-85093-P), Ministerio de Ciencia, Innovación y Universidades (RED2018-102387-T, PID2019-107268GB-100), Generalitat Valenciana (IDIFEDER/2021/013, GVA-COVID19/2021/079), MedalChemy S. L. (Medalchemy-22T), and the University of Alicante (VIGROB-068). |
| URI: | http://hdl.handle.net/10045/142152 |
| ISSN: | 0022-3263 (Print) | 1520-6904 (Online) |
| DOI: | 10.1021/acs.joc.4c00198 |
| Language: | eng |
| Type: | info:eu-repo/semantics/article |
| Rights: | © 2024 The Authors. Published by American Chemical Society. This publication is licensed under CC-BY 4.0. |
| Peer Review: | si |
| Publisher version: | https://doi.org/10.1021/acs.joc.4c00198 |
| Appears in Collections: | INV - SINTAS - Artículos de Revistas |
Files in This Item:
| File | Description | Size | Format | |
|---|---|---|---|---|
 Hernandez-Ibanez_etal_2024_JOrgChem.pdf | 2,37 MB | Adobe PDF | Open Preview | |
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