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Volumn , Issue 7, 2008, Pages 995-998

Phosphoric acid diesters as efficient catalysts for hydroaminations of nonactivated alkenes and an application to asymmetric hydroaminations

Author keywords

Alkenes; Amines; Asymmetric catalysis; Br nsted acids; Phosphates

Indexed keywords

ALKENE DERIVATIVE; BRONSTED ACID; PHOSPHORIC ACID DERIVATIVE; SOLVENT;

EID: 42949128240     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1072505     Document Type: Article
Times cited : (58)

References (47)
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    • Selected additional reviews: (a) Lee, A. V.; Schafer, L. L. Eur. J. Inorg. Chem. 2007, 2243.
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    • For acid-catalyzed hydroamidation reactions of olefins, which were found not applicable to more basic amines, see: Intramolecular: (a) Schlummer, B.; Hartwig, J. F. Org. Lett. 2002, 4, 1471.
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    • Intermolecular: (e) Li, Z.; Zhang, J.; Brouwer, C.; Yang, C.-G.; Reich, N. W.; He, C. Org. Lett. 2006, 8, 4175.
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    • and references cited therein. For the elegant use of 3,3′-bis(trisarylsilyl)-substituted binaphtholate rare-earth-metal catalysts in asymmetric hydroaminations, see
    • (i) For the elegant use of 3,3′-bis(trisarylsilyl)-substituted binaphtholate rare-earth-metal catalysts in asymmetric hydroaminations, see: Gribkov, D. V.; Hultzsch, K. C.; Hampel, F. J. Am. Chem. Soc. 2006, 128, 3748; and references cited therein.
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    • 4 gave only traces of the desired product.
    • 4 gave only traces of the desired product.
  • 45
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    • Representative Procedure: Synthesis of 2a (Table 3, Entry 1) A solution of 1a (162 mg, 0.495 mmol) and 3e (42.8 mg, 0.050 mmol) in dry Cl2HCCHCl2 (1.0 mL) was stirred under N2 for 23 h at 130°C. At ambient temperature sat. aq NaHCO3 (25 mL) and Et2O (50 mL) were added. The separated aqueous phase was extracted with Et2O (2 x 50 mL, The combined organic layers were dried over Na2SO4 and concentrated in vacuo. The remaining residue was purified by column chromatography on silica gel (n- pentane-Et2O, 15:1) to yield 2a (158 mg, 97, as a light yellow solid (mp 71.2-72.4°C, 1H NMR (300 MHz, CDCl 3, δ, 7.42-7.37 (m, 15 H, 4.12 (d, J, 13.3 Hz, 1 H, 3.70 (d, J, 10.0 Hz, 1 H, 3.30 (d, J, 13.3 Hz, 1 H, 2.99-2.83 (m, 3 H, 2.25 (dd, J, 12.2, 7.2 Hz, 1 H, 1.21 d, J, 6.1 Hz, 3 H
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    • Under these reaction conditions, there was no indication for catalyst decomposition, and primary aminoalkenes reacted less efficiently
    • Under these reaction conditions, there was no indication for catalyst decomposition, and primary aminoalkenes reacted less efficiently.
  • 47
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    • Enantiomerically enriched catalyst 3a provided, under otherwise identical reaction conditions, only racemic product.
    • Enantiomerically enriched catalyst 3a provided, under otherwise identical reaction conditions, only racemic product.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.