Rendering classical hydrophilic enantiopure Werner salts [M(en)3]n+nX- lipophilic (M/n = Cr/3, Co/3, Rh/3, Ir/3, Pt/4); new chiral hydrogen bond donor catalysts and enantioselectivities as a function of metal and charge
Maximuck WJ, Ganzmann C, Alvi S, Hooda KR, Gladysz JA (2020)
Publication Type: Journal article
Publication year: 2020
Journal
Book Volume: 49
Pages Range: 3680-3691
Journal Issue: 12
DOI: 10.1039/d0dt00523a
Abstract
Known hydrophilic halide salts of the title compounds are converted to new lipophilic BArf- (B(3,5-C6H3(CF3)2)4-) salts. These are isolated as hydrates (Λ- or Δ-[M(en)3]n+nBArf-·zH2O; z = 17-9) and characterized by NMR (acetone-d6) and microanalyses. Thermal stabilities are probed by capillary thermolyses and TGA and DSC measurements (onset of dehydration 71-151 °C). In the presence of tertiary amines, they are effective catalysts for enantioselective Michael type carbon-carbon or carbon-nitrogen bond forming additions of 1,3-dicarbonyl compounds (acceptors: trans-β-nitrostyrene, di-tert-butylazodicarboxylate, 2-cyclopenten-1-one; average ee = 33%, 52%, 17%). Effects of the metal and charge upon enantioselectivities are analyzed. A number of properties appear to correlate to the NH Brønsted acidity order ([Pt(en)3]4+ > [Cr(en)3]3+ > [Co(en)3]3+ > [Rh(en)3]3+ > [Ir(en)3]3+).
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APA:
Maximuck, W.J., Ganzmann, C., Alvi, S., Hooda, K.R., & Gladysz, J.A. (2020). Rendering classical hydrophilic enantiopure Werner salts [M(en)3]n+nX- lipophilic (M/n = Cr/3, Co/3, Rh/3, Ir/3, Pt/4); new chiral hydrogen bond donor catalysts and enantioselectivities as a function of metal and charge. Dalton Transactions, 49(12), 3680-3691. https://dx.doi.org/10.1039/d0dt00523a
MLA:
Maximuck, William J., et al. "Rendering classical hydrophilic enantiopure Werner salts [M(en)3]n+nX- lipophilic (M/n = Cr/3, Co/3, Rh/3, Ir/3, Pt/4); new chiral hydrogen bond donor catalysts and enantioselectivities as a function of metal and charge." Dalton Transactions 49.12 (2020): 3680-3691.
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