Highly regioselective construction of spirocycles via phosphine-catalyzed [3 + 2]-cycloaddition

Journal of Organic Chemistry

Volumn 67, Issue 25, 2002, Pages 8901-8905

  Du, Yishu ^a   Lu, Xiyan ^a   Yu, Yihua ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

REGIOSELECTIVITY;

ADDITION REACTIONS; CATALYSIS; SUBSTRATES;

ESTERS;

1,3 BUTADIENE DERIVATIVE; ALKANE DERIVATIVE; CARBENOID; HETEROCYCLIC COMPOUND; PHOSPHINE; SPIROCYCLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CYCLOADDITION; REACTION ANALYSIS; REACTION OPTIMIZATION; STEREOCHEMISTRY;

EID: 0037073879     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo026111t     Document Type: Article

References (41)

1. For reviews of spirocyclic compounds, see: (a) Heathcock, C. H. In The Total Synthesis of Natural Products; ApSimon, J., Ed.; Willey: New York, 1973; Vol. 2, pp 466 and 504. (b) Marshall, J. A.; Brady, S. F.; Andersen, N. H. Fortschr. Chem. Org. Naturst. 1974, 31, 283. (c) Martin, J. D. In Studies in Natural Products Chemistry Rahman, A. U., Ed.; Elsevier: Amsterdam, 1990; Vol. 6, p 59. (d) Sannigrahi, M. Tetrahedron 1999, 55, 9007 and references therein.
2. For reviews of spirocyclic compounds, see: (a) Heathcock, C. H. In The Total Synthesis of Natural Products; ApSimon, J., Ed.; Willey: New York, 1973; Vol. 2, pp 466 and 504. (b) Marshall, J. A.; Brady, S. F.; Andersen, N. H. Fortschr. Chem. Org. Naturst. 1974, 31, 283. (c) Martin, J. D. In Studies in Natural Products Chemistry Rahman, A. U., Ed.; Elsevier: Amsterdam, 1990; Vol. 6, p 59. (d) Sannigrahi, M. Tetrahedron 1999, 55, 9007 and references therein.
3. For reviews of spirocyclic compounds, see: (a) Heathcock, C. H. In The Total Synthesis of Natural Products; ApSimon, J., Ed.; Willey: New York, 1973; Vol. 2, pp 466 and 504. (b) Marshall, J. A.; Brady, S. F.; Andersen, N. H. Fortschr. Chem. Org. Naturst. 1974, 31, 283. (c) Martin, J. D. In Studies in Natural Products Chemistry Rahman, A. U., Ed.; Elsevier: Amsterdam, 1990; Vol. 6, p 59. (d) Sannigrahi, M. Tetrahedron 1999, 55, 9007 and references therein.
4. For reviews of spirocyclic compounds, see: (a) Heathcock, C. H. In The Total Synthesis of Natural Products; ApSimon, J., Ed.; Willey: New York, 1973; Vol. 2, pp 466 and 504. (b) Marshall, J. A.; Brady, S. F.; Andersen, N. H. Fortschr. Chem. Org. Naturst. 1974, 31, 283. (c) Martin, J. D. In Studies in Natural Products Chemistry Rahman, A. U., Ed.; Elsevier: Amsterdam, 1990; Vol. 6, p 59. (d) Sannigrahi, M. Tetrahedron 1999, 55, 9007 and references therein.
5. For some examples of the synthesis of spirocycles via [3 + 2]-cycloaddition reaction involving three-carbon synthons, see: (a) Danheiser, R. L.; Carini, D. J.; Basak, A. J. Am. Chem. Soc. 1981, 103, 1604. (b) Trost, B. M.; Acemoglu, M. Tetrahedron Lett. 1989, 30, 1495. (c) Trost, B. M.; King, S. A.; Schmidt, T. J. Am. Chem. Soc. 1989, 111, 5902. (d) Trost, B. M.; Yang, B.; Miller, M. L. J. Am. Chem. Soc. 1989, 111, 6482. (e) Trost, B. M.; Sharma, S.; Schmidt, T. J. Am. Chem. Soc. 1992, 114, 7903. (f) Trost, B. M.; Marrs, C. M. J. Am. Chem. Soc. 1993, 115, 6636. (g) Knolker, H.-J.; Jones, P. G.; Grafe, R. Synlett 1996, 1155. (h) Akiyama, T.; Hoshi, E.; Fujiyoshi, S. J. Chem. Soc., Perkin Trans. 1 1998, 2121. (i) Alper, P. B.; Meyers, C.; Lerchner, A.; Siegel, D. R.; Carreira, E. M. Angew. Chem., Int. Ed. 1999, 38, 3186.
6. For some examples of the synthesis of spirocycles via [3 + 2]-cycloaddition reaction involving three-carbon synthons, see: (a) Danheiser, R. L.; Carini, D. J.; Basak, A. J. Am. Chem. Soc. 1981, 103, 1604. (b) Trost, B. M.; Acemoglu, M. Tetrahedron Lett. 1989, 30, 1495. (c) Trost, B. M.; King, S. A.; Schmidt, T. J. Am. Chem. Soc. 1989, 111, 5902. (d) Trost, B. M.; Yang, B.; Miller, M. L. J. Am. Chem. Soc. 1989, 111, 6482. (e) Trost, B. M.; Sharma, S.; Schmidt, T. J. Am. Chem. Soc. 1992, 114, 7903. (f) Trost, B. M.; Marrs, C. M. J. Am. Chem. Soc. 1993, 115, 6636. (g) Knolker, H.-J.; Jones, P. G.; Grafe, R. Synlett 1996, 1155. (h) Akiyama, T.; Hoshi, E.; Fujiyoshi, S. J. Chem. Soc., Perkin Trans. 1 1998, 2121. (i) Alper, P. B.; Meyers, C.; Lerchner, A.; Siegel, D. R.; Carreira, E. M. Angew. Chem., Int. Ed. 1999, 38, 3186.
7. For some examples of the synthesis of spirocycles via [3 + 2]-cycloaddition reaction involving three-carbon synthons, see: (a) Danheiser, R. L.; Carini, D. J.; Basak, A. J. Am. Chem. Soc. 1981, 103, 1604. (b) Trost, B. M.; Acemoglu, M. Tetrahedron Lett. 1989, 30, 1495. (c) Trost, B. M.; King, S. A.; Schmidt, T. J. Am. Chem. Soc. 1989, 111, 5902. (d) Trost, B. M.; Yang, B.; Miller, M. L. J. Am. Chem. Soc. 1989, 111, 6482. (e) Trost, B. M.; Sharma, S.; Schmidt, T. J. Am. Chem. Soc. 1992, 114, 7903. (f) Trost, B. M.; Marrs, C. M. J. Am. Chem. Soc. 1993, 115, 6636. (g) Knolker, H.-J.; Jones, P. G.; Grafe, R. Synlett 1996, 1155. (h) Akiyama, T.; Hoshi, E.; Fujiyoshi, S. J. Chem. Soc., Perkin Trans. 1 1998, 2121. (i) Alper, P. B.; Meyers, C.; Lerchner, A.; Siegel, D. R.; Carreira, E. M. Angew. Chem., Int. Ed. 1999, 38, 3186.
8. For some examples of the synthesis of spirocycles via [3 + 2]-cycloaddition reaction involving three-carbon synthons, see: (a) Danheiser, R. L.; Carini, D. J.; Basak, A. J. Am. Chem. Soc. 1981, 103, 1604. (b) Trost, B. M.; Acemoglu, M. Tetrahedron Lett. 1989, 30, 1495. (c) Trost, B. M.; King, S. A.; Schmidt, T. J. Am. Chem. Soc. 1989, 111, 5902. (d) Trost, B. M.; Yang, B.; Miller, M. L. J. Am. Chem. Soc. 1989, 111, 6482. (e) Trost, B. M.; Sharma, S.; Schmidt, T. J. Am. Chem. Soc. 1992, 114, 7903. (f) Trost, B. M.; Marrs, C. M. J. Am. Chem. Soc. 1993, 115, 6636. (g) Knolker, H.-J.; Jones, P. G.; Grafe, R. Synlett 1996, 1155. (h) Akiyama, T.; Hoshi, E.; Fujiyoshi, S. J. Chem. Soc., Perkin Trans. 1 1998, 2121. (i) Alper, P. B.; Meyers, C.; Lerchner, A.; Siegel, D. R.; Carreira, E. M. Angew. Chem., Int. Ed. 1999, 38, 3186.
9. For some examples of the synthesis of spirocycles via [3 + 2]-cycloaddition reaction involving three-carbon synthons, see: (a) Danheiser, R. L.; Carini, D. J.; Basak, A. J. Am. Chem. Soc. 1981, 103, 1604. (b) Trost, B. M.; Acemoglu, M. Tetrahedron Lett. 1989, 30, 1495. (c) Trost, B. M.; King, S. A.; Schmidt, T. J. Am. Chem. Soc. 1989, 111, 5902. (d) Trost, B. M.; Yang, B.; Miller, M. L. J. Am. Chem. Soc. 1989, 111, 6482. (e) Trost, B. M.; Sharma, S.; Schmidt, T. J. Am. Chem. Soc. 1992, 114, 7903. (f) Trost, B. M.; Marrs, C. M. J. Am. Chem. Soc. 1993, 115, 6636. (g) Knolker, H.-J.; Jones, P. G.; Grafe, R. Synlett 1996, 1155. (h) Akiyama, T.; Hoshi, E.; Fujiyoshi, S. J. Chem. Soc., Perkin Trans. 1 1998, 2121. (i) Alper, P. B.; Meyers, C.; Lerchner, A.; Siegel, D. R.; Carreira, E. M. Angew. Chem., Int. Ed. 1999, 38, 3186.
10. For some examples of the synthesis of spirocycles via [3 + 2]-cycloaddition reaction involving three-carbon synthons, see: (a) Danheiser, R. L.; Carini, D. J.; Basak, A. J. Am. Chem. Soc. 1981, 103, 1604. (b) Trost, B. M.; Acemoglu, M. Tetrahedron Lett. 1989, 30, 1495. (c) Trost, B. M.; King, S. A.; Schmidt, T. J. Am. Chem. Soc. 1989, 111, 5902. (d) Trost, B. M.; Yang, B.; Miller, M. L. J. Am. Chem. Soc. 1989, 111, 6482. (e) Trost, B. M.; Sharma, S.; Schmidt, T. J. Am. Chem. Soc. 1992, 114, 7903. (f) Trost, B. M.; Marrs, C. M. J. Am. Chem. Soc. 1993, 115, 6636. (g) Knolker, H.-J.; Jones, P. G.; Grafe, R. Synlett 1996, 1155. (h) Akiyama, T.; Hoshi, E.; Fujiyoshi, S. J. Chem. Soc., Perkin Trans. 1 1998, 2121. (i) Alper, P. B.; Meyers, C.; Lerchner, A.; Siegel, D. R.; Carreira, E. M. Angew. Chem., Int. Ed. 1999, 38, 3186.
11. For some examples of the synthesis of spirocycles via [3 + 2]-cycloaddition reaction involving three-carbon synthons, see: (a) Danheiser, R. L.; Carini, D. J.; Basak, A. J. Am. Chem. Soc. 1981, 103, 1604. (b) Trost, B. M.; Acemoglu, M. Tetrahedron Lett. 1989, 30, 1495. (c) Trost, B. M.; King, S. A.; Schmidt, T. J. Am. Chem. Soc. 1989, 111, 5902. (d) Trost, B. M.; Yang, B.; Miller, M. L. J. Am. Chem. Soc. 1989, 111, 6482. (e) Trost, B. M.; Sharma, S.; Schmidt, T. J. Am. Chem. Soc. 1992, 114, 7903. (f) Trost, B. M.; Marrs, C. M. J. Am. Chem. Soc. 1993, 115, 6636. (g) Knolker, H.-J.; Jones, P. G.; Grafe, R. Synlett 1996, 1155. (h) Akiyama, T.; Hoshi, E.; Fujiyoshi, S. J. Chem. Soc., Perkin Trans. 1 1998, 2121. (i) Alper, P. B.; Meyers, C.; Lerchner, A.; Siegel, D. R.; Carreira, E. M. Angew. Chem., Int. Ed. 1999, 38, 3186.
12. For some examples of the synthesis of spirocycles via [3 + 2]-cycloaddition reaction involving three-carbon synthons, see: (a) Danheiser, R. L.; Carini, D. J.; Basak, A. J. Am. Chem. Soc. 1981, 103, 1604. (b) Trost, B. M.; Acemoglu, M. Tetrahedron Lett. 1989, 30, 1495. (c) Trost, B. M.; King, S. A.; Schmidt, T. J. Am. Chem. Soc. 1989, 111, 5902. (d) Trost, B. M.; Yang, B.; Miller, M. L. J. Am. Chem. Soc. 1989, 111, 6482. (e) Trost, B. M.; Sharma, S.; Schmidt, T. J. Am. Chem. Soc. 1992, 114, 7903. (f) Trost, B. M.; Marrs, C. M. J. Am. Chem. Soc. 1993, 115, 6636. (g) Knolker, H.-J.; Jones, P. G.; Grafe, R. Synlett 1996, 1155. (h) Akiyama, T.; Hoshi, E.; Fujiyoshi, S. J. Chem. Soc., Perkin Trans. 1 1998, 2121. (i) Alper, P. B.; Meyers, C.; Lerchner, A.; Siegel, D. R.; Carreira, E. M. Angew. Chem., Int. Ed. 1999, 38, 3186.
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