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Article << Previous     |     Next >>   Contents Vol 67(9)

Facial Selectivity in the Addition of Lithium Dimethylcuprate to 6-Substituted Tricyclo[5.2.1.02,6]deca-4,8-dienones. Synthesis of β-Substituted Cyclopentenones Using Flash Vacuum Thermolysis

Antonius J. H. Klunder A , Andries A. Volkers A and Binne Zwanenburg A B

A Radboud University Nijmegen, Institute for Molecules and Materials, Department of Organic Chemistry, Heyendaalseweg 135, 6525 AJ Nijmegen, The Netherlands.
B Corresponding author. Email: B.Zwanenburg@science.ru.nl

Australian Journal of Chemistry 67(9) 1243-1250 http://dx.doi.org/10.1071/CH14094
Submitted: 25 February 2014  Accepted: 6 April 2014   Published: 29 April 2014


 
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Abstract

The stereoselectivity of the nucleophilic addition of lithium dimethylcuprate and lithium di-n-pentylcuprate to 6-substituted tricyclo[5.2.1.02,6]deca-4,8-dienones was investigated. It was shown that substituents at the 6-position can either exert a steric effect or an electronic effect. Steric approach control predominantly giving the endo product was observed for 6-alkyl substituents. Stereoelectronic control could be adequately rationalised using the Cieplak model. Flash vacuum thermolysis was used to prepare a series of β-substituted cyclopentenoids. The sequence leading to cyclopentenoids has an attractive scope.





References

[1]  A. J. H. Klunder, J. Zhu, B. Zwanenburg, Chem. Rev. 1999, 99, 1163.
         | CrossRef | CAS |

[2]  For a review on retro-Diels-Alder reactions, see: B. Rickborn, Org. React. 1998, 52, 1.
         | CAS |

[3]  B. Zwanenburg, A. A. Volkers, A. J. H. Klunder, Aust. J. Chem. 2014, 67,
         | CrossRef |

[4]  (a) M. Revés, A. Lledó, Y. Li, E. Blasi, A. Riera, X. Verdaguer, Org. Lett. 2012, 14, 3534.
         | CrossRef | PubMed |
      (b) L. N. Mander, R. J. Thomsons, J. Org. Chem. 2005, 70, 1654.
         | CrossRef |
      (c) M. Iqbal, Y. Li, P. Evans, Tetrahedron 2004, 60, 2531.
         | CrossRef |
      (d) J. P. Eddolls, M. Iqbal, S. M. Roberts, M. G. Santor, Tetrahedron 2004, 60, 2539.
         | CrossRef |
      (e) J. Christoffers, T. Werner, W. Frey, A. Baro, Chem. – Eur. J. 2004, 10, 1042.
         | CrossRef |
      (f) M. Iqbal, P. Evans, Tetrahedron Lett. 2003, 44, 5741.
         | CrossRef |
      (g) T. J. Brocksom, J. Nakamura, M. L. Ferreira, U. Brocksom, J. Braz. Chem. Soc. 2001, 12, 597.
         | CrossRef |
      (h) G. Mehta, D. S. Reddy, J. Chem. Soc., Perkin Trans. 1 2001, I, 1153.
         | CrossRef |
      (i) J. Zhu, A. J. H. Klunder, B. Zwanenburg, Tetrahedron 1994, 50, 10597.
         | CrossRef |

[5]  P. M. M. A. Dols, M. M. H. Verstappen, A. J. H. Klunder, B. Zwanenburg, Tetrahedron 1993, 49, 11353.
         | CrossRef | CAS |

[6]  (a) W. H. Watson, A. Nagl, R. P. Kashyap, V. Vidyasagar, Acta Crystallogr. C 1990, 46, 1265.
         | CrossRef |
      (b) W. B. Smith, A. P. Marchand, S. C. Suri, P. W. Jin, J. Org. Chem. 1986, 51, 3052.
         | CrossRef |

[7]  J. Zhu, J. Van der Hoeven, J.-W. Slief, A. J. H. Klunder, B. Zwanenburg, Tetrahedron 1995, 51, 10953.
         | CrossRef | CAS |

[8]  (a) A. S. Cieplak, Chem. Rev. 1999, 99, 1265.
         | CrossRef | CAS | PubMed |
      (b) A. S. Cieplak, J. Am. Chem. Soc. 1981, 103, 4540.
         | CrossRef |
      (c) A. S. Cieplak, B. D. Tait, C. R. Johnson, J. Am. Chem. Soc. 1989, 111, 8447.
         | CrossRef |

[9]  A. A. Volkers, A. J. H. Klunder, B. Zwanenburg, Tetrahedron 2009, 65, 389.
         | CrossRef | CAS |

[10]  A. J. H. Klunder, W. B. Huizinga, P. J. M. Sessink, B. Zwanenburg, Tetrahedron Lett. 1987, 28, 357.
         | CrossRef | CAS |

[11]  A. J. H. Klunder, A. A. Volkers, B. Zwanenburg, Tetrahedron 2009, 65, 2356.
         | CrossRef | CAS |


   
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