Temperature-Controlled Stereodivergent Synthesis of 2,2'-Biflavanones promoted by Samarium Diiodide.

Author(s) Soto, M.; Soengas, R.G.; Silva, A.M.S.; Gotor-Fernández, V.; Solla, H.
Journal Chemistry
Date Published 2019 Jul 30
Abstract

We report herein the first example of a radical stereodivergent reaction directed towards the stereoselective synthesis of both (R*,R*)- and (R*,S*)-2,2'-biflavanones promoted by samarium diiodide. Control experiments showed that the selectivity of this reaction was exclusively controlled by the temperature. It was possible to generate a variety of 2,2'-biflavanones bearing different substitution patterns at the aromatic ring from good to quantitative yields, being both stereoisomers of the desired compounds obtained with total or high control of the selectivity. A mechanism that explains both, the generation of the corresponding 2,2'-biflavanones and their selectivity is also discussed. The structure and stereochemistry determination of each isomer was unequivocally elucidated by single crystal X-ray diffraction experiments.

DOI 10.1002/chem.201902927
ISSN 1521-3765
Citation Soto M, Soengas RG, Silva AM, Gotor-Fernández V, Solla H. Temperature-Controlled Stereodivergent Synthesis of 2,2'-Biflavanones promoted by Samarium Diiodide. Chemistry. 2019.

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