Electric Literature of C36H29O4P. Aromatic heterocyclic compounds can also be classified according to the number of heteroatoms contained in the heterocycle: single heteroatom, two heteroatoms, three heteroatoms and four heteroatoms. Compound: (11bR)-2,6-Bis(3,5-dimethylphenyl)-4-hydroxydinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepine 4-oxide, is researched, Molecular C36H29O4P, CAS is 861909-53-7, about Site-Selective Acylation of Natural Products with BINOL-Derived Phosphoric Acids. Author is Li, Junqi; Grosslight, Samantha; Miller, Scott J.; Sigman, Matthew S.; Toste, F. Dean.
The site-selective acylation of a steroidal natural product 19-hydroxydehydroepiandrosterone catalyzed by 1,1′-Bi(2-naphthol)-derived (BINOL) chiral phosphoric acids (CPAs) is described. Systematic variation and multivariate linear regression anal. reveal that the same steric parameters typically needed for high enantioselectivity with this class of CPAs are also required for site-selectivity in this case. D. functional theory calculations identify addnl. weak CH-π interactions as contributors to site discrimination. We further report a rare example of site-selective acylation of phenols through the evaluation of naringenin, a flavonoid natural product, using CPA catalysis. These results suggest that BINOL-derived CPAs may have broader applications in site-selective catalysis.
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