Aldol–Tishchenko Reaction of α-Oxy Ketones: Diastereoselective Synthesis of 1,2,3-Triol Derivatives
α-Oxy ketones, easily accessible by conventional routes, can be selectively deprotonated generating an enolate intermediate, which upon treatment with paraformaldehyde undergoes an aldol–Tishchenko reaction, leading to relevant 1,2,3-triol fragments in a totally diastereoselective manner. The excell...
| Authors: | ; ; ; |
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| Format: | Article |
| Status: | Accepted version |
| Publication date: | 2021 |
| Country: | España |
| Institution: | Universidad de Burgos (UBU) |
| Repository: | Repositorio Institucional de la Universidad de Burgos (RIUBU) |
| OAI Identifier: | oai:riubu.ubu.es:10259/6089 |
| Online Access: | http://hdl.handle.net/10259/6089 |
| Access Level: | Open access |
| Keyword: | aldol–Tishchenko reaction enolates α-oxy ketones polyol derivatives diastereoselectivity oxetanes Química orgánica Chemistry, Organic |
| Summary: | α-Oxy ketones, easily accessible by conventional routes, can be selectively deprotonated generating an enolate intermediate, which upon treatment with paraformaldehyde undergoes an aldol–Tishchenko reaction, leading to relevant 1,2,3-triol fragments in a totally diastereoselective manner. The excellent stereocontrol in the generation of a quaternary stereocenter is attributed to stereoelectronic effects in the Evans intermediate. This methodology allows overcoming some limitations of our previously reported strategy, based on the reaction of α-lithiobenzyl ethers with esters and paraformaldehyde, broadening the scope of the obtained polyols. Synthetic applications of this process include the preparation of a new dilignol model and some functionalized oxetanes. |
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