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Highly Efficient Asymmetric Direct Stoichiometric Aldol Reactions on/in Water
Author(s) -
Huang Junmin,
Zhang Xiaotong,
Armstrong Daniel W.
Publication year - 2007
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200703606
Subject(s) - aldol reaction , cyclohexanone , stoichiometry , chemistry , aryl , catalysis , cyclodextrin , combinatorial chemistry , organic chemistry , alkyl
Hydrophobic pocket pleaser : A novel asymmetric catalytic system in water mediated by sulfated β‐cyclodextrin (see picture) can bind the organocatalyst tert ‐butylphenoxyproline and associated hydrophobic reactants. Enantio‐ and diastereoselectivities up to >99 % and close to quantitative yields could be achieved for stoichiometric direct aldol reactions of cyclohexanone and aryl aldehydes with this system.