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Chiral Ytterbium Complex-Catalyzed Direct Asymmetric Aldol-Tishchenko Reaction: Synthesis of anti-1,3-Diols

✍ Scribed by Jacek Mlynarski; Bartosz Rakiel; Maciej Stodulski; Agata Suszczyńska; Jadwiga Frelek

Publisher: John Wiley and Sons
Year: 2006
Tongue: English
Weight: 198 KB
Volume: 12
Category: Article
ISSN: 0947-6539
DOI: 10.1002/chem.200600357

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✦ Synopsis

Abstract

The asymmetric aldol‐Tishchenko reaction of aromatic aldehydes with aliphatic and aromatic ketones has been developed as an efficient strategy for the synthesis of anti‐1,3‐diols in good yield with high diastereocontrol and good levels of enantioselectivity. This domino‐type reaction is catalyzed by a chiral ytterbium complex that promotes both the aldol reaction through enolization of the carbonyl compound and the Evans–Tishchenko reduction of the aldol intermediate. The stereochemistry of the resulting diols is also investigated and finally proved by using CD techniques.

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