Portal de Periódicos da CAPES

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

2005; Wiley; Volume: 44; Issue: 20 Linguagem: Inglês

10.1002/anie.200500408

1521-3773

Taichi Kano, Jun Takai, Osamu Tokuda, Keiji Maruoka,

Molecular spectroscopy and chirality

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. Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2005/z500408_s.pdf or from the author. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.