A Facile Cycloisomerization for the Formation of Medium and Large Rings via Allenes

Angewandte Chemie (International Edition in English)

Volumn 36, Issue 16, 1997, Pages 1750-1753

  Trost, Barry M ^a   Michellys, Pierre Yves ^a   Gerusz, Vincent J ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

Cyclizations; Lactams; Lactones; Macrocycles; Palladium

Indexed keywords

EID: 0030800450     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199717501     Document Type: Article

References (26)

1. Selected overviews: B. Dietrich, P. Viout, J. M. Lehn, Macrocyclic Chemistry, VCH, Weinheim, 1993; Macrolide Antibiotics, Chemistry, Biology, and Practice (Ed.: S. Omura), Academic Press, New York, 1984; Proteinase Inhibitors (Eds.: A. J. Barret, G. Salvensen), Elsevier, Amsterdam, 1986.
2. Selected overviews: B. Dietrich, P. Viout, J. M. Lehn, Macrocyclic Chemistry, VCH, Weinheim, 1993; Macrolide Antibiotics, Chemistry, Biology, and Practice (Ed.: S. Omura), Academic Press, New York, 1984; Proteinase Inhibitors (Eds.: A. J. Barret, G. Salvensen), Elsevier, Amsterdam, 1986.
3. Selected overviews: B. Dietrich, P. Viout, J. M. Lehn, Macrocyclic Chemistry, VCH, Weinheim, 1993; Macrolide Antibiotics, Chemistry, Biology, and Practice (Ed.: S. Omura), Academic Press, New York, 1984; Proteinase Inhibitors (Eds.: A. J. Barret, G. Salvensen), Elsevier, Amsterdam, 1986.
4. Recent examples: B. Greve, P. Imming, S. Laufer, Angew. Chem. 1996, 108, 1312; Angew. Chem. Int. Ed. Engl. 1996, 35, 1221; L. Zhang, J. A. Pesti, T. D. Costello, P. J. Sheeran, R. Uyeda, P. Ma, G. S. Kauffman, R. Ward, J. L. McMillan, J. Org. Chem. 1996, 61, 5180; T. L. Hendrickson, J. R. Spencer, M. Kato, B. Imperiali, J. Am. Chem. Soc. 1996, 118, 7636; R. Haubner, W. Schmitt, G. Hölzemann, S. L. Goodman, A. Jonczyk, H. Kessler, ibid. 1996, 118, 7881.
5. Recent examples: B. Greve, P. Imming, S. Laufer, Angew. Chem. 1996, 108, 1312; Angew. Chem. Int. Ed. Engl. 1996, 35, 1221; L. Zhang, J. A. Pesti, T. D. Costello, P. J. Sheeran, R. Uyeda, P. Ma, G. S. Kauffman, R. Ward, J. L. McMillan, J. Org. Chem. 1996, 61, 5180; T. L. Hendrickson, J. R. Spencer, M. Kato, B. Imperiali, J. Am. Chem. Soc. 1996, 118, 7636; R. Haubner, W. Schmitt, G. Hölzemann, S. L. Goodman, A. Jonczyk, H. Kessler, ibid. 1996, 118, 7881.
6. Recent examples: B. Greve, P. Imming, S. Laufer, Angew. Chem. 1996, 108, 1312; Angew. Chem. Int. Ed. Engl. 1996, 35, 1221; L. Zhang, J. A. Pesti, T. D. Costello, P. J. Sheeran, R. Uyeda, P. Ma, G. S. Kauffman, R. Ward, J. L. McMillan, J. Org. Chem. 1996, 61, 5180; T. L. Hendrickson, J. R. Spencer, M. Kato, B. Imperiali, J. Am. Chem. Soc. 1996, 118, 7636; R. Haubner, W. Schmitt, G. Hölzemann, S. L. Goodman, A. Jonczyk, H. Kessler, ibid. 1996, 118, 7881.
7. Recent examples: B. Greve, P. Imming, S. Laufer, Angew. Chem. 1996, 108, 1312; Angew. Chem. Int. Ed. Engl. 1996, 35, 1221; L. Zhang, J. A. Pesti, T. D. Costello, P. J. Sheeran, R. Uyeda, P. Ma, G. S. Kauffman, R. Ward, J. L. McMillan, J. Org. Chem. 1996, 61, 5180; T. L. Hendrickson, J. R. Spencer, M. Kato, B. Imperiali, J. Am. Chem. Soc. 1996, 118, 7636; R. Haubner, W. Schmitt, G. Hölzemann, S. L. Goodman, A. Jonczyk, H. Kessler, ibid. 1996, 118, 7881.
8. Recent examples: B. Greve, P. Imming, S. Laufer, Angew. Chem. 1996, 108, 1312; Angew. Chem. Int. Ed. Engl. 1996, 35, 1221; L. Zhang, J. A. Pesti, T. D. Costello, P. J. Sheeran, R. Uyeda, P. Ma, G. S. Kauffman, R. Ward, J. L. McMillan, J. Org. Chem. 1996, 61, 5180; T. L. Hendrickson, J. R. Spencer, M. Kato, B. Imperiali, J. Am. Chem. Soc. 1996, 118, 7636; R. Haubner, W. Schmitt, G. Hölzemann, S. L. Goodman, A. Jonczyk, H. Kessler, ibid. 1996, 118, 7881.
9. Selected reviews: C. J. Roxburgh, Tetrahedron 1995, 51, 9767; H. Stach, M. Hesse, ibid, 1988, 44, 1573; M. A. Titus, Chem. Rev. 1988, 88, 719; I. Paterson, M. M. Mansuri, Tetrahedron 1985, 41, 3569 . Leading reference on the use of ring-closing metathesis (RCM) for macrocyclizations: A. Fürstner, K. Langemann, J. Org. Chem. 1996, 61, 3942 and references therein (slow additions of the substrates were employed). Conformational constraints facilitate RCM and may be required in some cases: S. J. Miller, S.-H. Kim, Z. R. Chen, R. H. Grubbs, J. Am. Chem. Soc. 1995, 117, 2108.
10. Selected reviews: C. J. Roxburgh, Tetrahedron 1995, 51, 9767; H. Stach, M. Hesse, ibid, 1988, 44, 1573; M. A. Titus, Chem. Rev. 1988, 88, 719; I. Paterson, M. M. Mansuri, Tetrahedron 1985, 41, 3569 . Leading reference on the use of ring-closing metathesis (RCM) for macrocyclizations: A. Fürstner, K. Langemann, J. Org. Chem. 1996, 61, 3942 and references therein (slow additions of the substrates were employed). Conformational constraints facilitate RCM and may be required in some cases: S. J. Miller, S.-H. Kim, Z. R. Chen, R. H. Grubbs, J. Am. Chem. Soc. 1995, 117, 2108.
11. Selected reviews: C. J. Roxburgh, Tetrahedron 1995, 51, 9767; H. Stach, M. Hesse, ibid, 1988, 44, 1573; M. A. Titus, Chem. Rev. 1988, 88, 719; I. Paterson, M. M. Mansuri, Tetrahedron 1985, 41, 3569 . Leading reference on the use of ring-closing metathesis (RCM) for macrocyclizations: A. Fürstner, K. Langemann, J. Org. Chem. 1996, 61, 3942 and references therein (slow additions of the substrates were employed). Conformational constraints facilitate RCM and may be required in some cases: S. J. Miller, S.-H. Kim, Z. R. Chen, R. H. Grubbs, J. Am. Chem. Soc. 1995, 117, 2108.
12. Selected reviews: C. J. Roxburgh, Tetrahedron 1995, 51, 9767; H. Stach, M. Hesse, ibid, 1988, 44, 1573; M. A. Titus, Chem. Rev. 1988, 88, 719; I. Paterson, M. M. Mansuri, Tetrahedron 1985, 41, 3569 . Leading reference on the use of ring-closing metathesis (RCM) for macrocyclizations: A. Fürstner, K. Langemann, J. Org. Chem. 1996, 61, 3942 and references therein (slow additions of the substrates were employed). Conformational constraints facilitate RCM and may be required in some cases: S. J. Miller, S.-H. Kim, Z. R. Chen, R. H. Grubbs, J. Am. Chem. Soc. 1995, 117, 2108.
13. Selected reviews: C. J. Roxburgh, Tetrahedron 1995, 51, 9767; H. Stach, M. Hesse, ibid, 1988, 44, 1573; M. A. Titus, Chem. Rev. 1988, 88, 719; I. Paterson, M. M. Mansuri, Tetrahedron 1985, 41, 3569 . Leading reference on the use of ring-closing metathesis (RCM) for macrocyclizations: A. Fürstner, K. Langemann, J. Org. Chem. 1996, 61, 3942 and references therein (slow additions of the substrates were employed). Conformational constraints facilitate RCM and may be required in some cases: S. J. Miller, S.-H. Kim, Z. R. Chen, R. H. Grubbs, J. Am. Chem. Soc. 1995, 117, 2108.
14. Selected reviews: C. J. Roxburgh, Tetrahedron 1995, 51, 9767; H. Stach, M. Hesse, ibid, 1988, 44, 1573; M. A. Titus, Chem. Rev. 1988, 88, 719; I. Paterson, M. M. Mansuri, Tetrahedron 1985, 41, 3569 . Leading reference on the use of ring-closing metathesis (RCM) for macrocyclizations: A. Fürstner, K. Langemann, J. Org. Chem. 1996, 61, 3942 and references therein (slow additions of the substrates were employed). Conformational constraints facilitate RCM and may be required in some cases: S. J. Miller, S.-H. Kim, Z. R. Chen, R. H. Grubbs, J. Am. Chem. Soc. 1995, 117, 2108.
15. B. M. Trost, V. J. Gerusz, J. Am. Chem. Soc. 1995, 117, 5156.
16. For related work proposing a carbapalladation mechanism, see Y. Yamamoto, M. Al-Masum, N. Asao, J. Am. Chem. Soc. 1994, 116, 6019; Y. Yamamoto, M. Al-Masum, N. Fujiwara, N. Asao, Tetrahedron Lett. 1995, 36, 2811 . More recently, Yamamoto et al. have adopted our proposed hydropalladation mechanism as more consistent for some of their cases: Y. Yamamoto, M. Al-Masum, A. Takeda, Chem. Commun. 1996, 831; M. Meguro, S. Kamijo, Y. Yamamoto, Tetrahedron Lett. 1996, 37, 7453.
17. For related work proposing a carbapalladation mechanism, see Y. Yamamoto, M. Al-Masum, N. Asao, J. Am. Chem. Soc. 1994, 116, 6019; Y. Yamamoto, M. Al-Masum, N. Fujiwara, N. Asao, Tetrahedron Lett. 1995, 36, 2811 . More recently, Yamamoto et al. have adopted our proposed hydropalladation mechanism as more consistent for some of their cases: Y. Yamamoto, M. Al-Masum, A. Takeda, Chem. Commun. 1996, 831; M. Meguro, S. Kamijo, Y. Yamamoto, Tetrahedron Lett. 1996, 37, 7453.
18. For related work proposing a carbapalladation mechanism, see Y. Yamamoto, M. Al-Masum, N. Asao, J. Am. Chem. Soc. 1994, 116, 6019; Y. Yamamoto, M. Al-Masum, N. Fujiwara, N. Asao, Tetrahedron Lett. 1995, 36, 2811 . More recently, Yamamoto et al. have adopted our proposed hydropalladation mechanism as more consistent for some of their cases: Y. Yamamoto, M. Al-Masum, A. Takeda, Chem. Commun. 1996, 831; M. Meguro, S. Kamijo, Y. Yamamoto, Tetrahedron Lett. 1996, 37, 7453.
19. For related work proposing a carbapalladation mechanism, see Y. Yamamoto, M. Al-Masum, N. Asao, J. Am. Chem. Soc. 1994, 116, 6019; Y. Yamamoto, M. Al-Masum, N. Fujiwara, N. Asao, Tetrahedron Lett. 1995, 36, 2811 . More recently, Yamamoto et al. have adopted our proposed hydropalladation mechanism as more consistent for some of their cases: Y. Yamamoto, M. Al-Masum, A. Takeda, Chem. Commun. 1996, 831; M. Meguro, S. Kamijo, Y. Yamamoto, Tetrahedron Lett. 1996, 37, 7453.
20. Cyclization of ω-haloallenes: S. Ma, E. Negishi, J. Am. Chem. Soc. 1995, 117, 6345.
21. B. M. Trost, L. Zhi, Tetrahedron Lett. 1992, 33, 1831.
22. All new compounds have been fully characterized by spectroscopy and elemental analysis (composition determined by high-resolution mass spectrometry and/or combustion analysis).
23. A. C. Cope, P. T. Moore, W. R. Moore, J. Am. Chem. Soc. 1959, 81, 3153.
24. C. Galli, G. Illuminati, L. Mandolini, P. Tamborra, J. Am. Chem. Soc. 1977, 99, 2591.
25. However, cf. B. M. Trost, T. R. Verhoeven, J. Am. Chem. Soc. 1980, 102, 4743.
26. E. P. Johnson, G.-P. Chen, K. R. Fales, B. E. Lenk, R. J. Szendroi, X.-J. Wang, J. A. Carlson, J. Org. Chem. 1995, 60, 6595.