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An easy and straightforward approach to the asymmetric synthesis of isoflavanones

✍ Scribed by Jose L. Vicario; Dolores Badı́a; Luisa Carrillo


Publisher
Elsevier Science
Year
2003
Tongue
English
Weight
203 KB
Volume
14
Category
Article
ISSN
0957-4166

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✦ Synopsis


Isoflavanones 4a-d have been prepared in a stereocontrolled fashion using (S,S)-(+)-pseudoephedrine as a chiral auxiliary. The employed synthetic pathway consists of only four steps and involves initial formation of the stereogenic centre via diastereoselective aldol reaction of pseudoephedrine arylacetamides 1a-c with formaldehyde, followed by aryl ether formation under Mitsunobu conditions, removal of the chiral auxiliary by hydrolysis and final Friedel-Crafts intramolecular acylation.


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