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Chiral Ytterbium Complex‐Catalyzed Direct Asymmetric Aldol‐Tishchenko Reaction: Synthesis of anti ‐1,3‐Diols
Author(s) -
Mlynarski Jacek,
Rakiel Bartosz,
Stodulski Maciej,
Suszczyńska Agata,
Frelek Jadwiga
Publication year - 2006
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200600357
Subject(s) - aldol reaction , chemistry , keto–enol tautomerism , enantioselective synthesis , catalysis , yield (engineering) , ytterbium , organic chemistry , materials science , optoelectronics , doping , metallurgy
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.