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Diastereoselective synthesis of syn-3,5-dihydroxyesters via ruthenium-catalyzed asymmetric transfer hydrogenation
✍ Scribed by Kathelyne Everaere; Nicolas Franceschini; André Mortreux; Jean-François Carpentier
- Publisher
- Elsevier Science
- Year
- 2002
- Tongue
- French
- Weight
- 66 KB
- Volume
- 43
- Category
- Article
- ISSN
- 0040-4039
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📜 SIMILAR VOLUMES
1,3-Diketones were reduced to 1,3-diols by using RuCl[N-(tosyl)-1,2-(diphenylethylenediamine) (h 6 -arene)] in the presence of formic acid and triethylamine. 1,3-Diols were obtained in good chemical yields and with high ee when symmetrical diketones were reduced.
An efficient synthesis of the natural occuring amino acid (2S.3R)-3-hydroxylysine is reported. The five step sequence features a highly enantioselective dynamic kinetic resolution of racemic o~acetamido [J-keto phtidimidohexanoate using ruthenium(ll) catalyzed hydrogenation reaction.
The enantioselective ruthenium promoted hydrogenation of beta-keto ester, derived from (S)- or (R)-proline and (S)-pipecolic acid, provided a new efficient route to hydroxylated pyrrolizidine or indolizidine ring systems in diastereomeric excesses up to 99%. A practical synthesis of (+)-alpha-conhyd