Bennett, Steven H. published the artcileDifunctionalization of C-C σ-Bonds Enabled by the Reaction of Bicyclo[1.1.0]butyl Boronate Complexes with Electrophiles: Reaction Development, Scope, and Stereochemical Origins, Category: alcohols-buliding-blocks, the publication is Journal of the American Chemical Society (2020), 142(39), 16766-16775, database is CAplus and MEDLINE.
Difunctionalization reactions of C-C σ-bonds have the potential to streamline access to mols. that would otherwise be difficult to prepare However, the development of such reactions is challenging because C-C σ-bonds are typically unreactive. Exploiting the high ring-strain energy of polycyclic carbocycles is a common strategy to weaken and facilitate the reaction of C-C σ-bonds, but there are limited examples of highly strained C-C σ-bonds being used in difunctionalization reactions. We demonstrate that highly strained bicyclo[1.1.0]butyl boronate complexes (strain energy ca. 65 kcal/mol), which were prepared by reacting boronic esters with bicyclo[1.1.0]butyl lithium, react with electrophiles to achieve the diastereoselective difunctionalization of the strained central C-C σ-bond of the bicyclo[1.1.0]butyl unit. The reaction shows broad substrate scope, with a range of different electrophiles and boronic esters being successfully employed to form a diverse set of 1,1,3-trisubstituted cyclobutanes (>50 examples) with high diastereoselectivity. The high diastereoselectivity observed has been rationalized based on a combination of exptl. data and DFT calculations, which suggests that sep. concerted and stepwise reaction mechanisms are operating, depending upon the migrating substituent and electrophile used.
Journal of the American Chemical Society published new progress about 608534-44-7. 608534-44-7 belongs to alcohols-buliding-blocks, auxiliary class Other Aromatic,Boronic acid and ester,Boronate Esters,Boronic Acids,Boronic acid and ester, name is 2-(2,3-Dihydro-1H-inden-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, and the molecular formula is C15H21BO2, Category: alcohols-buliding-blocks.
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