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Design of an Axially Chiral Amino Acid with a Binaphthyl Backbone as an Organocatalyst for a Direct Asymmetric Aldol Reaction
Author(s) -
Kano Taichi,
Takai Jun,
Tokuda Osamu,
Maruoka Keiji
Publication year - 2005
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.200500408
Subject(s) - aldol reaction , chemistry , axial symmetry , organic chemistry , stereochemistry , catalysis , physics , quantum mechanics
A robust binaphthyl‐based amino acid (( S )‐ 1 ) exhibits higher stability and selectivity than proline for the catalysis of a direct asymmetric aldol reaction between aldehydes and acetone (see scheme; DMF= N , N ‐dimethylformamide). Olefinic, heteroaromatic, and aromatic aldehydes were found to be suitable substrates, with the corresponding aldol adducts being obtained in good yields and excellent enantioselectivities.