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  • Silver-catalyzed asymmetric synthesis of 2,3-dihydrobenzofurans: a new chiral synthesis of pterocarpans.

Silver-catalyzed asymmetric synthesis of 2,3-dihydrobenzofurans: a new chiral synthesis of pterocarpans.

Chemistry (Weinheim an der Bergstrasse, Germany) (2006-09-06)
Leticia Jiménez-González, Sergio García-Muñoz, Miriam Alvarez-Corral, Manuel Muñoz-Dorado, Ignacio Rodríguez-García
ABSTRACT

2,3-Dihydrobenzofurans can be diastereoselectively prepared by condensation of aromatic aldehydes with 2,3-dihydrobenzoxasilepines under the catalysis of Ag(I) complexes, and in the presence of a source of fluoride ion. The application of this strategy by using chiral catalysts leads to a new enantioselective total synthesis of natural cis-pterocarpans and their trans isomers. Through this method, the first enantioselective total synthesis of the antifungal agent (-)-pterocarpin was achieved. In addition, a new entry into the heteroaromatic system of 2,5-dihydrobenzoxepine is also presented.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
2,3-Dihydrobenzofuran, 99%