A titanacycle-to-carbocycle relay leading to an expedient synthesis of cyclopentadienois

Angewandte Chemie - International Edition

Volumn 38, Issue 23, 1999, Pages 3516-3518

  Urabe, Hirokazu ^a   Narita, Miho ^a   Sato, Fumie ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

Alkynes; Cyclizations; Cyclopentadienes metallacycles; Titanium

Indexed keywords

ALKYNE; CYCLOPENTADIENE DERIVATIVE; TITANIUM;

ARTICLE; CHEMICAL BINDING; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; SYNTHESIS;

EID: 0033521222     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19991203)38:23<3516::AID-ANIE3516>3.0.CO;2-0     Document Type: Article

References (38)

1. Reviews: S. L. Buchwald, R. B. Nielsen, Chem. Rev. 1988, 88, 1047-1058; E. Negishi in Comprehensive Organic Synthesis, Vol. 5 (Eds.: B. M. Trost, I. Fleming). Pergamon, Oxford, 1991, pp. 1163-1184; R. D. Broene, S. L. Buchwald, Science 1993, 261, 1696-1701; E. Negishi, T. Takahashi, Acc. Chem. Res. 1994, 27, 124-130; M. Maier in Organic Synthesis Highlights II (Ed.: H. Waldmann), VCH, Weinheim, 1995, pp. 99-113; A. Ohff, S. Pulst, C. Lefeber, N. Peulecke, P. Arndt, V. V. Burkalov, U. Rosenthal, Synlett 1996, 111-118; E. Negishi, T. Takahashi, Bull. Chem. Soc. Jpn. 1998, 71, 755-764.
2. Reviews: S. L. Buchwald, R. B. Nielsen, Chem. Rev. 1988, 88, 1047- 1058; E. Negishi in Comprehensive Organic Synthesis, Vol. 5 (Eds.: B. M. Trost, I. Fleming). Pergamon, Oxford, 1991, pp. 1163-1184; R. D. Broene, S. L. Buchwald, Science 1993, 261, 1696-1701; E. Negishi, T. Takahashi, Acc. Chem. Res. 1994, 27, 124-130; M. Maier in Organic Synthesis Highlights II (Ed.: H. Waldmann), VCH, Weinheim, 1995, pp. 99-113; A. Ohff, S. Pulst, C. Lefeber, N. Peulecke, P. Arndt, V. V. Burkalov, U. Rosenthal, Synlett 1996, 111-118; E. Negishi, T. Takahashi, Bull. Chem. Soc. Jpn. 1998, 71, 755-764.
3. Reviews: S. L. Buchwald, R. B. Nielsen, Chem. Rev. 1988, 88, 1047- 1058; E. Negishi in Comprehensive Organic Synthesis, Vol. 5 (Eds.: B. M. Trost, I. Fleming). Pergamon, Oxford, 1991, pp. 1163-1184; R. D. Broene, S. L. Buchwald, Science 1993, 261, 1696-1701; E. Negishi, T. Takahashi, Acc. Chem. Res. 1994, 27, 124-130; M. Maier in Organic Synthesis Highlights II (Ed.: H. Waldmann), VCH, Weinheim, 1995, pp. 99-113; A. Ohff, S. Pulst, C. Lefeber, N. Peulecke, P. Arndt, V. V. Burkalov, U. Rosenthal, Synlett 1996, 111-118; E. Negishi, T. Takahashi, Bull. Chem. Soc. Jpn. 1998, 71, 755-764.
4. Reviews: S. L. Buchwald, R. B. Nielsen, Chem. Rev. 1988, 88, 1047- 1058; E. Negishi in Comprehensive Organic Synthesis, Vol. 5 (Eds.: B. M. Trost, I. Fleming). Pergamon, Oxford, 1991, pp. 1163-1184; R. D. Broene, S. L. Buchwald, Science 1993, 261, 1696-1701; E. Negishi, T. Takahashi, Acc. Chem. Res. 1994, 27, 124-130; M. Maier in Organic Synthesis Highlights II (Ed.: H. Waldmann), VCH, Weinheim, 1995, pp. 99-113; A. Ohff, S. Pulst, C. Lefeber, N. Peulecke, P. Arndt, V. V. Burkalov, U. Rosenthal, Synlett 1996, 111-118; E. Negishi, T. Takahashi, Bull. Chem. Soc. Jpn. 1998, 71, 755-764.
5. Reviews: S. L. Buchwald, R. B. Nielsen, Chem. Rev. 1988, 88, 1047- 1058; E. Negishi in Comprehensive Organic Synthesis, Vol. 5 (Eds.: B. M. Trost, I. Fleming). Pergamon, Oxford, 1991, pp. 1163-1184; R. D. Broene, S. L. Buchwald, Science 1993, 261, 1696-1701; E. Negishi, T. Takahashi, Acc. Chem. Res. 1994, 27, 124-130; M. Maier in Organic Synthesis Highlights II (Ed.: H. Waldmann), VCH, Weinheim, 1995, pp. 99-113; A. Ohff, S. Pulst, C. Lefeber, N. Peulecke, P. Arndt, V. V. Burkalov, U. Rosenthal, Synlett 1996, 111-118; E. Negishi, T. Takahashi, Bull. Chem. Soc. Jpn. 1998, 71, 755-764.
6. Reviews: S. L. Buchwald, R. B. Nielsen, Chem. Rev. 1988, 88, 1047- 1058; E. Negishi in Comprehensive Organic Synthesis, Vol. 5 (Eds.: B. M. Trost, I. Fleming). Pergamon, Oxford, 1991, pp. 1163-1184; R. D. Broene, S. L. Buchwald, Science 1993, 261, 1696-1701; E. Negishi, T. Takahashi, Acc. Chem. Res. 1994, 27, 124-130; M. Maier in Organic Synthesis Highlights II (Ed.: H. Waldmann), VCH, Weinheim, 1995, pp. 99-113; A. Ohff, S. Pulst, C. Lefeber, N. Peulecke, P. Arndt, V. V. Burkalov, U. Rosenthal, Synlett 1996, 111-118; E. Negishi, T. Takahashi, Bull. Chem. Soc. Jpn. 1998, 71, 755-764.
7. Reviews: S. L. Buchwald, R. B. Nielsen, Chem. Rev. 1988, 88, 1047- 1058; E. Negishi in Comprehensive Organic Synthesis, Vol. 5 (Eds.: B. M. Trost, I. Fleming). Pergamon, Oxford, 1991, pp. 1163-1184; R. D. Broene, S. L. Buchwald, Science 1993, 261, 1696-1701; E. Negishi, T. Takahashi, Acc. Chem. Res. 1994, 27, 124-130; M. Maier in Organic Synthesis Highlights II (Ed.: H. Waldmann), VCH, Weinheim, 1995, pp. 99-113; A. Ohff, S. Pulst, C. Lefeber, N. Peulecke, P. Arndt, V. V. Burkalov, U. Rosenthal, Synlett 1996, 111-118; E. Negishi, T. Takahashi, Bull. Chem. Soc. Jpn. 1998, 71, 755-764.
8. O. Geis, H.-G. Schmalz, Angew. Chem. 1998, 110, 955-958; Angew. Chem. Im. Ed. 1998, 37, 911-914; S. C. Berk, R. B. Grossman, S. L. Buchwald, J. Am. Chem. Soc. 1994, 116, 8593-8601; F. A. Hicks, S. L. Buchwald, J. Am. Chem. Soc. 1996, 118, 11688-11689; J. Barluenga, R. Sanz, F. J. Fañańs, Chem. Eur. J. 1997, 1324-1336; T. Takahashi, S. Huo, R. Hara, Y. Noguchi, K. Nakajima, W.-H. Sun, J. Am. Chem. Soc. 1999, 121, 1094-1095.
9. O. Geis, H.-G. Schmalz, Angew. Chem. 1998, 110, 955-958; Angew. Chem. Im. Ed. 1998, 37, 911-914; S. C. Berk, R. B. Grossman, S. L. Buchwald, J. Am. Chem. Soc. 1994, 116, 8593-8601; F. A. Hicks, S. L. Buchwald, J. Am. Chem. Soc. 1996, 118, 11688-11689; J. Barluenga, R. Sanz, F. J. Fañańs, Chem. Eur. J. 1997, 1324-1336; T. Takahashi, S. Huo, R. Hara, Y. Noguchi, K. Nakajima, W.-H. Sun, J. Am. Chem. Soc. 1999, 121, 1094-1095.
10. O. Geis, H.-G. Schmalz, Angew. Chem. 1998, 110, 955-958; Angew. Chem. Im. Ed. 1998, 37, 911-914; S. C. Berk, R. B. Grossman, S. L. Buchwald, J. Am. Chem. Soc. 1994, 116, 8593-8601; F. A. Hicks, S. L. Buchwald, J. Am. Chem. Soc. 1996, 118, 11688-11689; J. Barluenga, R. Sanz, F. J. Fañańs, Chem. Eur. J. 1997, 1324-1336; T. Takahashi, S. Huo, R. Hara, Y. Noguchi, K. Nakajima, W.-H. Sun, J. Am. Chem. Soc. 1999, 121, 1094-1095.
11. O. Geis, H.-G. Schmalz, Angew. Chem. 1998, 110, 955-958; Angew. Chem. Im. Ed. 1998, 37, 911-914; S. C. Berk, R. B. Grossman, S. L. Buchwald, J. Am. Chem. Soc. 1994, 116, 8593-8601; F. A. Hicks, S. L. Buchwald, J. Am. Chem. Soc. 1996, 118, 11688-11689; J. Barluenga, R. Sanz, F. J. Fañańs, Chem. Eur. J. 1997, 1324-1336; T. Takahashi, S. Huo, R. Hara, Y. Noguchi, K. Nakajima, W.-H. Sun, J. Am. Chem. Soc. 1999, 121, 1094-1095.
12. O. Geis, H.-G. Schmalz, Angew. Chem. 1998, 110, 955-958; Angew. Chem. Im. Ed. 1998, 37, 911-914; S. C. Berk, R. B. Grossman, S. L. Buchwald, J. Am. Chem. Soc. 1994, 116, 8593-8601; F. A. Hicks, S. L. Buchwald, J. Am. Chem. Soc. 1996, 118, 11688-11689; J. Barluenga, R. Sanz, F. J. Fañańs, Chem. Eur. J. 1997, 1324-1336; T. Takahashi, S. Huo, R. Hara, Y. Noguchi, K. Nakajima, W.-H. Sun, J. Am. Chem. Soc. 1999, 121, 1094-1095.
13. O. Geis, H.-G. Schmalz, Angew. Chem. 1998, 110, 955-958; Angew. Chem. Im. Ed. 1998, 37, 911-914; S. C. Berk, R. B. Grossman, S. L. Buchwald, J. Am. Chem. Soc. 1994, 116, 8593-8601; F. A. Hicks, S. L. Buchwald, J. Am. Chem. Soc. 1996, 118, 11688-11689; J. Barluenga, R. Sanz, F. J. Fañańs, Chem. Eur. J. 1997, 1324-1336; T. Takahashi, S. Huo, R. Hara, Y. Noguchi, K. Nakajima, W.-H. Sun, J. Am. Chem. Soc. 1999, 121, 1094-1095.
14. H. Urabe, T. Hata, F. Sato, Tetrahedron Lett. 1995, 36, 4261-4264; H. Urabe, T. Takeda, D. Hideura, F. Sato, J. Am. Chem. Soc. 1997, 119, 11245-11305.
15. H. Urabe, T. Hata, F. Sato, Tetrahedron Lett. 1995, 36, 4261-4264; H. Urabe, T. Takeda, D. Hideura, F. Sato, J. Am. Chem. Soc. 1997, 119, 11245-11305.
16. Z. Zhao, Y. Ding, G. Zhao, J. Org. Chem. 1998, 63, 9285-9291.
17. To execute this process, transmetalation of the aforementioned Group 4 metallacycles to other appropriate organometallic intermediates (typically a copper reagent) has sometimes been undertaken: Y. Liu, B. Shen, M. Kotora, T. Takahashi, Angew. Chem. 1999. 111, 966-968; Angew. Chem. Int. Ed. 1999, 38, 949-951; M. Kotora, C. Xi, T. Takahashi, Tetrahedron Lett. 1998, 39, 4321-4324. Alternatively, a stepwise sequence by the use of bis-halogenated intermediates that are readily available by the halogenolysis of the metallacycles has also been devised: E. Negishi, S. Ma, T. Sugihara, Y. Noda, J. Org. Chem. 1997, 62, 1922-1923.
18. To execute this process, transmetalation of the aforementioned Group 4 metallacycles to other appropriate organometallic intermediates (typically a copper reagent) has sometimes been undertaken: Y. Liu, B. Shen, M. Kotora, T. Takahashi, Angew. Chem. 1999. 111, 966-968; Angew. Chem. Int. Ed. 1999, 38, 949-951; M. Kotora, C. Xi, T. Takahashi, Tetrahedron Lett. 1998, 39, 4321-4324. Alternatively, a stepwise sequence by the use of bis-halogenated intermediates that are readily available by the halogenolysis of the metallacycles has also been devised: E. Negishi, S. Ma, T. Sugihara, Y. Noda, J. Org. Chem. 1997, 62, 1922-1923.
19. To execute this process, transmetalation of the aforementioned Group 4 metallacycles to other appropriate organometallic intermediates (typically a copper reagent) has sometimes been undertaken: Y. Liu, B. Shen, M. Kotora, T. Takahashi, Angew. Chem. 1999. 111, 966-968; Angew. Chem. Int. Ed. 1999, 38, 949-951; M. Kotora, C. Xi, T. Takahashi, Tetrahedron Lett. 1998, 39, 4321-4324. Alternatively, a stepwise sequence by the use of bis-halogenated intermediates that are readily available by the halogenolysis of the metallacycles has also been devised: E. Negishi, S. Ma, T. Sugihara, Y. Noda, J. Org. Chem. 1997, 62, 1922-1923.
20. To execute this process, transmetalation of the aforementioned Group 4 metallacycles to other appropriate organometallic intermediates (typically a copper reagent) has sometimes been undertaken: Y. Liu, B. Shen, M. Kotora, T. Takahashi, Angew. Chem. 1999. 111, 966-968; Angew. Chem. Int. Ed. 1999, 38, 949-951; M. Kotora, C. Xi, T. Takahashi, Tetrahedron Lett. 1998, 39, 4321-4324. Alternatively, a stepwise sequence by the use of bis-halogenated intermediates that are readily available by the halogenolysis of the metallacycles has also been devised: E. Negishi, S. Ma, T. Sugihara, Y. Noda, J. Org. Chem. 1997, 62, 1922-1923.
21. H. Urabe, F. Sato, J. Org. Chem. 1996, 61, 6756-6757; S. Yamaguchi, R.-Z. Jin, K. Tamao, F. Sato, Org. Chem. 1998, 63, 10060-10062; H. Urabe, F. Sato, J. Am. Chem. Soc. 1999, 121, 1245-1255: H. Urabe, J. Synth. Org. Chem. Jpn. 1999, 57, 492-502.
22. H. Urabe, F. Sato, J. Org. Chem. 1996, 61, 6756-6757; S. Yamaguchi, R.-Z. Jin, K. Tamao, F. Sato, Org. Chem. 1998, 63, 10060-10062; H. Urabe, F. Sato, J. Am. Chem. Soc. 1999, 121, 1245-1255: H. Urabe, J. Synth. Org. Chem. Jpn. 1999, 57, 492-502.
23. H. Urabe, F. Sato, J. Org. Chem. 1996, 61, 6756-6757; S. Yamaguchi, R.-Z. Jin, K. Tamao, F. Sato, Org. Chem. 1998, 63, 10060-10062; H. Urabe, F. Sato, J. Am. Chem. Soc. 1999, 121, 1245-1255: H. Urabe, J. Synth. Org. Chem. Jpn. 1999, 57, 492-502.
24. H. Urabe, F. Sato, J. Org. Chem. 1996, 61, 6756-6757; S. Yamaguchi, R.-Z. Jin, K. Tamao, F. Sato, Org. Chem. 1998, 63, 10060-10062; H. Urabe, F. Sato, J. Am. Chem. Soc. 1999, 121, 1245-1255: H. Urabe, J. Synth. Org. Chem. Jpn. 1999, 57, 492-502.
25. T. Hamada, D. Suzuki, H. Urabe, F. Sato, J. Am. Chem. Soc. 1999, 121, 7342-7344.
26. F. Sato, H. Urabe, S. Okamoto, J. Synth. Org. Chem. Jpn. 1998, 56, 424-432.
27. Review on tandem reactions: R. A. Bunce, Tetrahedron 1995, 48, 13103-13159; P. J. Parsons, C. S. Penkett, A. J. Shell, Chem. Rev. 1996, 96, 195-206.
28. Review on tandem reactions: R. A. Bunce, Tetrahedron 1995, 48, 13103-13159; P. J. Parsons, C. S. Penkett, A. J. Shell, Chem. Rev. 1996, 96, 195-206.
29. Intramolecular addition of alkenyltitanium species to esters to yield ketones has been reported: S. Okamoto, A. Kasatkin, P. K. Zubaidha, F. Sato, J. Am. Chem. Soc. 1996, 118, 2208-2216; H. Urabe, K. Suzuki, F. Sato, J. Am. Chem. Soc. 1997, 119, 10014-10027.
30. Intramolecular addition of alkenyltitanium species to esters to yield ketones has been reported: S. Okamoto, A. Kasatkin, P. K. Zubaidha, F. Sato, J. Am. Chem. Soc. 1996, 118, 2208-2216; H. Urabe, K. Suzuki, F. Sato, J. Am. Chem. Soc. 1997, 119, 10014-10027.
31. Recent reports on the synthesis of cyclopentadienols and related cyclopentadienylamines: S. H. Hong, Y. K. Chung, Tetrahedron Lett. 1998, 39, 4843-4846; L. G. Quan,V. Gevorgyan,Y. Yamamoto, J. Am. Chem. Soc. 1999, 121, 3545-3546; R. Aumann, A. G. Meyer, R. Fröhlich, Organometallics 1996, 15, 5018-5027.
32. Recent reports on the synthesis of cyclopentadienols and related cyclopentadienylamines: S. H. Hong, Y. K. Chung, Tetrahedron Lett. 1998, 39, 4843-4846; L. G. Quan,V. Gevorgyan,Y. Yamamoto, J. Am. Chem. Soc. 1999, 121, 3545-3546; R. Aumann, A. G. Meyer, R. Fröhlich, Organometallics 1996, 15, 5018-5027.
33. Recent reports on the synthesis of cyclopentadienols and related cyclopentadienylamines: S. H. Hong, Y. K. Chung, Tetrahedron Lett. 1998, 39, 4843-4846; L. G. Quan,V. Gevorgyan,Y. Yamamoto, J. Am. Chem. Soc. 1999, 121, 3545-3546; R. Aumann, A. G. Meyer, R. Fröhlich, Organometallics 1996, 15, 5018-5027.
34. B. J. Wakefield, Organolithium Methods, Academic Press, London, 1988, p. 53; B. H. Lipshutz, S. Sengupta, in Organic Reactions, Vol. 41 (Ed.: L. A. Paquette), Wiley, New York, 1992, pp. 135-631.
35. B. J. Wakefield, Organolithium Methods, Academic Press, London, 1988, p. 53; B. H. Lipshutz, S. Sengupta, in Organic Reactions, Vol. 41 (Ed.: L. A. Paquette), Wiley, New York, 1992, pp. 135-631.
36. Condensed five- and six-membercd rings are frequently found in naturally occurring products. Review on the synthesis of polyquinanes: G. Mehta, A. Srikrishna. Chem. Rev. 1997, 97, 671-719; V. Singh, B. Thomas, Tetrahedron 1998, 54, 3647-3692; review on the synthesis of hydrindane rings: P. Jankowski, S. Marczak, J. Wicha, Tetrahedron 1998, 54, 12071-12150.
37. Condensed five- and six-membercd rings are frequently found in naturally occurring products. Review on the synthesis of polyquinanes: G. Mehta, A. Srikrishna. Chem. Rev. 1997, 97, 671-719; V. Singh, B. Thomas, Tetrahedron 1998, 54, 3647-3692; review on the synthesis of hydrindane rings: P. Jankowski, S. Marczak, J. Wicha, Tetrahedron 1998, 54, 12071-12150.
38. Condensed five- and six-membercd rings are frequently found in naturally occurring products. Review on the synthesis of polyquinanes: G. Mehta, A. Srikrishna. Chem. Rev. 1997, 97, 671-719; V. Singh, B. Thomas, Tetrahedron 1998, 54, 3647-3692; review on the synthesis of hydrindane rings: P. Jankowski, S. Marczak, J. Wicha, Tetrahedron 1998, 54, 12071-12150.