A facile synthesis of spiro-cyclopentenones from various 1-alkynes and cyclic exo-methylene compounds by intermolecular Pauson-Khand reaction

Heterocycles

Volumn 55, Issue 8, 2001, Pages 1439-1442

  Ishizaki, Miyuki ^a   Kasama, Yasuhiro ^a   Zyo, Mieko ^a   Niimi, Yuka ^a   Hoshino, Osamu ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001683334     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-01-9252     Document Type: Article

References (18)

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2. For some recent examples, (a) J.-C. Quiron, D. S. Grierson, J. Royer, and H.-P. Husson, Tetrahedron Lett., 1988, 29, 3311. (b) M. T. Crimmins, Z. Wang, and L. A. McKerlie, Tetrahedron Lett., 1996, 37, 8703.
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10. 3·MeBr, t-BuOK, THF, rt) in 98 and 83% yield, respectively.
11. 13C-NMR, IR, and MS spectral data.
12. +) 361.1678, found: 361.1676.
13. T. Sugihara, M. Yamada, M. Yamaguchi, and M. Nishizawa, Synlett, 1999, 771.
14. S. Shambayati, W. E. Crowe, and S. L. Schreiber, Tetrahedron Lett., 1990, 31, 5289.
15. N. E. Shore, 'The Pauson-Khand Cycloaddition Reaction for Synthesis of Cyclopentanones' in Organic Reactions, Vol. 40, John Wiley & Sons Inc., New York, 1991, p. 6: The reaction of phenylacetylene with simple alkene such as cyclohexene (2 eq.) in boiling toluene gave the corresponding adduct in only 3% yield; I. U. Khand and P. L. Pauson, J. Chem. Res. (M), 1977, 168.
16. N. E. Shore, 'The Pauson-Khand Cycloaddition Reaction for Synthesis of Cyclopentanones' in Organic Reactions, Vol. 40, John Wiley & Sons Inc., New York, 1991, p. 6: The reaction of phenylacetylene with simple alkene such as cyclohexene (2 eq.) in boiling toluene gave the corresponding adduct in only 3% yield; I. U. Khand and P. L. Pauson, J. Chem. Res. (M), 1977, 168.
17. The authors thank a referee for his useful suggestion: T. Sugihara, H. Ban, and M. Yamaguchi, J. Organometal. Chem., 1998, 554, 163.
18. The reaction of 4-aminophenylacetylene with 2a gave the corresponding adduct (3kN) in only 16% yield.