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Enantioselective O-allylic alkylation of Morita-Baylis-Hillman carbonates with oxime

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Abstract

The enantioselective O-allylic alkylation of acetophenone oxime with various Morita-Baylis-Hillman (MBH) carbonates has been accomplished by the catalysis of a commercially available cinchona alkaloid (DHQD)2PHAL. The corresponding O-allylic products were obtained in moderate to excellent yields up to 96% ee.

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References

  1. Hassner A, Patchornik G, Pradhan T K, Kumareswaran R. Intermolecular electrophilic O-amination of alcohols, J Org Chem, 2007, 72(2): 658–661

    Article  CAS  Google Scholar 

  2. Miyabe H, Matsumura A, Moriyama K, Takemoto Y. Utility of the iridium complex of the Pybox ligand in regio- and enantioselective allylic substitution. Org Lett, 2004, 6(24): 4631–4634

    Article  CAS  Google Scholar 

  3. Brouwer M S, Grosscurt A C. Benzoylurea compounds, and pesticidal and pharmaceutical compositions comprising same. US Patent 4609676, 1986-09-02

  4. Mordi M N, Pelta M D, Boote V, Morris G A, Barber J. Acid-catalyzed degradation of clarithromycin and erythromycin B: A comparative study using NMR spectroscopy. J Med Chem, 2000, 43(3): 467–474

    Article  CAS  Google Scholar 

  5. Gharbi-Benarous J, Delaforge M, Jankowski C K, Girault J P. A comparative NMR study between the macrolide antibiotic roxithromycin and erythromycin A with different biological properties. J Med Chem, 1991, 34(3): 1117–1125

    Article  CAS  Google Scholar 

  6. Dijk J V, Zwagemakers J M A. Oxime ether derivatives, a new class of nonsteroidal antiinflammatory compounds. J Med Chem, 1977, 20(9): 1199–1206

    Article  Google Scholar 

  7. Wahbi Y, Caujolle R, Tournaire C, Payard M, Linas M D, Seguela J P. Aromatic ethers of 1-aryl 2-(1H-azolyl)ethanol: Study of antifungal activity. Eur J Med Chem, 1995, 30(12): 955–962

    Article  CAS  Google Scholar 

  8. Vanderwal C D, Jacobsen E N. Enantioselective formal hydration of α,β-unsaturated imides by Al-catalyzed conjugate addition of oxime nucleophiles. J Am Chem Soc, 2004, 126(45): 14724–14725

    Article  CAS  Google Scholar 

  9. Chang L, Shang D J, Xin J G, Liu X H, Feng X M. Chiral N,N′-dioxide-iron(II) complexes catalyzed enantioselective oxa-Michael addition of α,β-unsaturated aldehydes. Tetrahedron Lett, 2008, 49(47): 6663–6666

    Article  CAS  Google Scholar 

  10. Dinér P, Nielsen M, Bertelsen S, Niess B, Jørgensen K A. Enantioselective hydroxylation of nitroalkenes: An organocatalytic approach. Chem Commun, 2007 (35): 3646–3648

  11. Bertelsen S, Dinér P, Johansen R L, Jørgensen K A. Asymmetric organocatalytic hydroxylation of α,β-unsaturated aldehydes. J Am Chem Soc, 2007, 129(6): 1536–1537

    Article  CAS  Google Scholar 

  12. Carlone A, Bartoli G, Bosco M, Pesciaioli F, Ricci P, Sambri L, Melchiorre P. Organocatalytic asymmetric β-hydroxylation of α,β-unsaturated ketones. Eur J Org Chem, 2007(3), 5492–5495

  13. Trost B M, Toste F D. Asymmetric O- and C-alkylation of phenols. J Am Chem Soc, 1998, 120(4): 815–816; Trost B M, Tsui H C, Toste F D. Deracemization of Baylis-Hillman adducts. J Am Chem Soc, 2000, 122(14): 3534–3535

    Article  CAS  Google Scholar 

  14. Kim J N, Lee H J, Gong J H. Synthesis of enantiomerically enriched Baylis-Hillman alcohols from their acetates: combination of kinetic resolution during the salt formation with (DHQD)2PHAL and following asymmetric induction during hydrolysis with NaHCO3 as a water surrogate. Tetrahedron Lett, 2002, 43(50): 9141–9146

    Article  CAS  Google Scholar 

  15. Du Y S, Han X L, Lu X Y. Alkaloids-catalyzed regio- and enantioselective allylic nucleophilic substitution of tert-butyl carbonate of the Morita-Baylis-Hillman products. Tetrahedron Lett, 2004, 45(25): 4967–4971

    Article  CAS  Google Scholar 

  16. Zhang T Z, Dai L X, Hou X L. Enantioselective allylic substitution of Morita-Baylis-Hillman adducts catalyzed by planar chiral [2.2] paracyclophane monophosphines. Tetrahedron: Asymmetry, 2007, 18(16): 1990–1994

    Article  CAS  Google Scholar 

  17. Jiang Y Q, Shi Y L, Shi M. Chiral phosphine-catalyzed enantioselective construction of γ-butenolides through substitution of Morita-Baylis-Hillman acetates with 2-trimethylsilyloxy furan. J Am Chem Soc, 2008, 130(23): 7202–7203

    Article  CAS  Google Scholar 

  18. Ma G N, Cao S H, Shi M. Chiral phosphine-catalyzed regio- and enantioselective allylic amination of Morita-Baylis-Hillman acetates. Tetrahedron: Asymmetry, 2009, 20(9): 1086–1092.

    Article  CAS  Google Scholar 

  19. Cui H L, Peng J, Feng X, Du W, Jiang K, Chen Y C. Dual organocatalysis: asymmetric allylic-allylic alkylation of α,α-dicyanoalkenes and Morita-Baylis-Hillman carbonates. Chem Eur J, 2009, 15(7): 1574–1577

    Article  CAS  Google Scholar 

  20. Jain N, Kumar A, Chauhan S M S. Metalloporphyrin and heteropoly acid catalyzed oxidation of C=NOH bonds in an ionic liquid: biomimetic models of nitric oxide synthase. Tetrahedron Lett, 2005, 46(15): 2599–2602

    Article  CAS  Google Scholar 

  21. Feng J, Lu X, Kong A, Han X. A highly regio- and stereo-selective [3+2] annulation of allylic compounds and 2-substituted 1,1-dicyanoalkenes through a catalytic carbon-phosphorus ylide reaction. Tetrahedron, 2007, 63(26): 6035–6041

    Article  CAS  Google Scholar 

  22. Marcelli T, van Maarseveen J H, Hiemstra H. Cupreines and Cupreidines: An emerging class of bifunctional cinchona organocatalysts. Angew Chem Int Ed, 2006, 45(45): 7496–7504

    Article  CAS  Google Scholar 

  23. Drewes S E, Emslie N D, Field J S, Khan A A, Ramesat N. Synthesis, resolution and assignment of absolute configuration of 2-(α-hydroxy)aryl acrylate esters. Tetrahedron: Asymmetry, 1992, 3(2): 255–260

    Article  CAS  Google Scholar 

  24. Basavaiah D, Rao K V, Reddy R J. The Baylis-Hillman reaction: a novel source of attraction, opportunities, and challenges in synthetic chemistry. Chem Soc Rev, 2007, 36(10): 1581–1588

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Key Laboratory of Drug-Targeting and Drug Delivery System of Education Ministry, Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu, 610041, China

    ZeKai Hu, HaiLei Cui, Kun Jiang & YingChun Chen

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  1. ZeKai Hu
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  2. HaiLei Cui
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  3. Kun Jiang
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  4. YingChun Chen
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Correspondence to YingChun Chen.

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Supported by the National Natural Science Foundation of China (Grant No. 20772084)

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Hu, Z., Cui, H., Jiang, K. et al. Enantioselective O-allylic alkylation of Morita-Baylis-Hillman carbonates with oxime. Sci. China Ser. B-Chem. 52, 1309–1313 (2009). https://doi.org/10.1007/s11426-009-0187-8

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  • DOI: https://doi.org/10.1007/s11426-009-0187-8

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