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.; Rodríguez-Solla, H.
Journal Chemistry
Date Published 2019 Oct 11
Abstract

In this work, 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 is reported. 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 in good-to-quantitative yields, being both stereoisomers of the desired compounds obtained with total or high control of selectivity. A mechanism that explains both the generation of the corresponding 2,2'-biflavanones and the 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, Rodríguez-Solla H. Temperature-Controlled Stereodivergent Synthesis of 2,2'-Biflavanones Promoted by Samarium Diiodide. Chemistry. 2019;25(57):13104-13108.

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