Design of an Axially Chiral Amino Acid with a Binaphthyl Backbone as an Organocatalyst for a Direct Asymmetric Aldol Reaction | Zendy

Kano Taichi | Zendy; Takai Jun | Zendy; Tokuda Osamu | Zendy; Maruoka Keiji | Zendy

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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.

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