Alvaro Valdés-Maqueda, Manuel Plaza, Carlos Valdes
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引用次数: 0
Abstract
The reactions of cyclic α,β-unsaturated N-tosylhydrazones and alkylboronic acids promoted by 370-390 nm light in the presence of a base give rise to allylic boronic acids that can be trapped as the corresponding pinacolboronates by treatment with pinacol. This reaction features wide scope regarding both coupling partners and functional group tolerance, allowing for the incorporation of a variety of natural product-derived fragments. The allylic boronic acids can be also reacted in a one-pot process with aldehydes, to produce homoallylic alcohols with very high diastereoselectivity. A three-component one-pot procedure has been developed revealing that the methodology is a powerful tool for the generation of structural diversity that is accomplished by incorporation of an ample variety of each of the three elements. Moreover, from a synthetic perspective, in the reaction, the formation of two C-C bonds, at the carbonyl and the β positions of a α,β-unsaturated carbonyl, has been achieved in the three-component reaction.
期刊介绍:
Chemical Science is a journal that encompasses various disciplines within the chemical sciences. Its scope includes publishing ground-breaking research with significant implications for its respective field, as well as appealing to a wider audience in related areas. To be considered for publication, articles must showcase innovative and original advances in their field of study and be presented in a manner that is understandable to scientists from diverse backgrounds. However, the journal generally does not publish highly specialized research.