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Site-selective and regioselective Diels–Alder reaction of allenyl aryl ethers

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Abstract

The site-selectivity and regioselectivity of Diels–Alder reactions of allenyl aryl ethers with cyclopentadiene and acrolein were studied. While cyclopentadiene (as an electron-rich diene) only reacted with the external double bond of allenyl aryl ethers to provide the site-selective normal electron demand Diels–Alder cycloadducts, acrolein (as an electron-deficient diene) reacted with the C1–C2 π bond of allenyl aryl ethers to provide the site- and regioselective hetero-Diels–Alder cycloadducts as exclusive products.

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References

  1. Heathcock CH, Graham SL, Pirrung MC, Plavec F, White CT (1983). In: Apsimon JW (ed) The total synthesis of natural products, vol 5. Wiley, New York

  2. Gibbs RA, Bartels K, Lee RWK, Okamura WH (1989) J Am Chem Soc 111:3717

    Article  CAS  Google Scholar 

  3. Hayakawa K, Nishiyama H, Kanematsu K (1985) J Org Chem 50:512

    Article  CAS  Google Scholar 

  4. Oppolzer W, Chapius C (1983) Tetrahedron Lett 24:4665

    Article  CAS  Google Scholar 

  5. Dolbier WR (1991) Adv Detail React Mech 1:127

    CAS  Google Scholar 

  6. Fleming I (1982) Frontier orbitals and organic chemical reactions. Wiley, London

    Google Scholar 

  7. Ishar MPS, Wali A, Gandhi IRP (1990) J Chem Soc Perkin Trans 1 2185

  8. Ismail ZM, Hoffmann HMR (1981) J Org Chem 46:3549

    Article  CAS  Google Scholar 

  9. Pasto DJ (1980) Tetrahedron Lett 21:4787

    Article  CAS  Google Scholar 

  10. Pledger H (1960) J Org Chem 25:278

    Article  CAS  Google Scholar 

  11. Murakami M, Matsuda T (2004). In: Krause N, Hashmi ASK (eds) Modern allene chemistry. Wiley-VCH, New York, vol 2, pp 727–815

  12. Padwa A, Bullock WH, Kline DN, Perumattam J (1989) J Org Chem 54:2862

    Article  CAS  Google Scholar 

  13. Padwa A, Meske M, Ni Z (1993) Tetrahedron Lett 34:5047

    Article  CAS  Google Scholar 

  14. Piperno A, Rescifina A, Corsaro A, Chiacchio MA, Procopio A, Romeo R (2007) Eur J Org Chem 1517

  15. Broggini G, Zecchi G (1996) Gazz Chim Ital 126:479

    CAS  Google Scholar 

  16. Padwa A, Matzinger M, Tomioka Y, Venkatramanan MK (1988) J Org Chem 53:955

    Article  CAS  Google Scholar 

  17. Parpani P, Zecchi G (1987) J Org Chem 52:1417

    Article  CAS  Google Scholar 

  18. Dolbier WR Jr, Wicks GE, Burkholder CR (1987) J Org Chem 52:2196

    Article  CAS  Google Scholar 

  19. Conrads M, Mattay J, Runsink J (1989) Chem Ber 122:2207

    Article  CAS  Google Scholar 

  20. Padwa A, Bullock WH, Norman BH, Perumattam J (1991) J Org Chem 56:4252

    Article  CAS  Google Scholar 

  21. Scheufler F, Maier ME (2000) Eur J Org Chem 3945–3948

  22. González-Gómez Á, Añorbe L, Poblador A, Domínguez G, Pérez-Castells J (2008) Eur J Org Chem 1370

  23. Moghaddam FM, Emami R (1997) Synth Commun 27:4073

    Article  CAS  Google Scholar 

  24. Klop W, Klusener PAA, Brandsma L (1984) Recl J R Neth Chem Soc 103:27

    CAS  Google Scholar 

  25. Wei LL, Xiong H, Douglas CJ, Hsung RP (1999) Tetrahedron Lett 40:6903

    Article  CAS  Google Scholar 

Download references

Acknowledgments

We are grateful to Dr. S. Taheri and Miss Z. Karimnia for recording NMR spectra. Also, we would like to acknowledge the Islamic Development Bank (IDB) for granting a loan in 1993 for purchasing a 500 MHz Bruker NMR spectrometer.

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Authors and Affiliations

  1. Laboratory of Organic Synthesis and Natural Products, Department of Chemistry, Sharif University of Technology, P. O. Box 11155-9516, Tehran, Iran

    Firouz Matloubi Moghaddam & Mostafa Kiamehr

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  1. Firouz Matloubi Moghaddam
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  2. Mostafa Kiamehr
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Correspondence to Firouz Matloubi Moghaddam.

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Moghaddam, F.M., Kiamehr, M. Site-selective and regioselective Diels–Alder reaction of allenyl aryl ethers. Monatsh Chem 141, 1333–1337 (2010). https://doi.org/10.1007/s00706-010-0406-1

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  • DOI: https://doi.org/10.1007/s00706-010-0406-1

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