Rhodium-catalyzed cycloisomerization of allenenes via metalacycle intermediates

Tetrahedron Letters

Volumn 44, Issue 33, 2003, Pages 6335-6338

  Makino, Tatsuya ^a   Itoh, Kenji ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALLENE DERIVATIVE; CYCLOPENTANE DERIVATIVE; HETEROCYCLIC COMPOUND; METAL DERIVATIVE; RHODIUM COMPLEX;

ARTICLE; CATALYSIS; CONFORMATION; CYCLIZATION; ELIMINATION REACTION; GAS CHROMATOGRAPHY; ISOMERISM;

EID: 0042848783     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01461-8     Document Type: Article

References (46)

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10. For leading papers in the last decade, see: Ti: (a) Thorn, M. G.; Hill, J. E.; Waratuke, S. A.; Johnson, E. S.; Franwick, P. E.; Rothwell, I. P. J. Am. Chem. Soc. 1997, 119, 8630-8641; (b) Okamoto, S.; Livinghouse, T. J. Am. Chem. Soc. 2000, 122, 1223-1224; (c) Okamoto, S.; Livinghouse, T. Organometallics 2000, 19, 1449-1451. Zr: (d) Christoffers, J.; Bergman, R. G. J. Am. Chem. Soc. 1996, 118, 4715-4716; (e) Thiele, S.; Erker, G. Ber./Recl. 1997, 130, 201-207; (f) Bazan, G. C.; Rodriguez, G.; Ashe, A. J., III; Al-Ahmad, S.; Kampf, J. W. Organometallics 1997, 16, 2492-2494; (g) Schweder, B.; Walther, D.; Döhler, T.; Klobes, O.; Görls, H. J. Prakt. Chem. 1999, 341, 736-747. Ru: (h) Yamamoto, Y.; Ohkoshi, N.; Itoh, K. J. Org. Chem. 1999, 64, 2178-2179; (i) Yamamoto, Y.; Nakagai, Y.; Ohkoshi, N.; Itoh, K. J. Am. Chem. Soc. 2001, 123, 6372-6380. Ni: (j) Radetich, B.; RajanBabu, T. V. J. Am. Chem. Soc. 1998, 120, 8007-8008; (k) Walther, D.; Döhler, T.; Heubach, K.; Klobes, O.; Schweder, B.; Görls, H. Z. Anorg. Allg. Chem. 1999, 625, 923-932. Pd: (l) Heumann, A.; Moukhliss, M. Synlett 1998, 1211-1212; (m) Widenhoefer, R. A.; Perch, N. S. Org. Lett. 1999, 1, 1103-1105; (n) Kisanga, P.; Widenhoefer, R. A. J. Am. Chem. Soc. 2000, 122, 10017-10026; (o) Bray, K. L.; Fairlamb, I. J. S.; Lloyd-Jones, G. C. Chem. Commun 2001, 187-188; (p) Kisanga, P.; Goj, L. A.; Widenhoefer, R. A. J. Org. Chem. 2001, 66, 635-637; (q) Oh, C. H.; Kim, J. D.; Han, J. W. Chem. Lett. 2001, 1290-1291; (r) Goj, L. A.; Widenhoefer, R. A. J. Am. Chem. Soc. 2001, 123, 11133-11147.
11. For leading papers in the last decade, see: Ti: (a) Thorn, M. G.; Hill, J. E.; Waratuke, S. A.; Johnson, E. S.; Franwick, P. E.; Rothwell, I. P. J. Am. Chem. Soc. 1997, 119, 8630-8641; (b) Okamoto, S.; Livinghouse, T. J. Am. Chem. Soc. 2000, 122, 1223-1224; (c) Okamoto, S.; Livinghouse, T. Organometallics 2000, 19, 1449-1451. Zr: (d) Christoffers, J.; Bergman, R. G. J. Am. Chem. Soc. 1996, 118, 4715-4716; (e) Thiele, S.; Erker, G. Ber./Recl. 1997, 130, 201-207; (f) Bazan, G. C.; Rodriguez, G.; Ashe, A. J., III; Al-Ahmad, S.; Kampf, J. W. Organometallics 1997, 16, 2492-2494; (g) Schweder, B.; Walther, D.; Döhler, T.; Klobes, O.; Görls, H. J. Prakt. Chem. 1999, 341, 736-747. Ru: (h) Yamamoto, Y.; Ohkoshi, N.; Itoh, K. J. Org. Chem. 1999, 64, 2178-2179; (i) Yamamoto, Y.; Nakagai, Y.; Ohkoshi, N.; Itoh, K. J. Am. Chem. Soc. 2001, 123, 6372-6380. Ni: (j) Radetich, B.; RajanBabu, T. V. J. Am. Chem. Soc. 1998, 120, 8007-8008; (k) Walther, D.; Döhler, T.; Heubach, K.; Klobes, O.; Schweder, B.; Görls, H. Z. Anorg. Allg. Chem. 1999, 625, 923-932. Pd: (l) Heumann, A.; Moukhliss, M. Synlett 1998, 1211-1212; (m) Widenhoefer, R. A.; Perch, N. S. Org. Lett. 1999, 1, 1103-1105; (n) Kisanga, P.; Widenhoefer, R. A. J. Am. Chem. Soc. 2000, 122, 10017-10026; (o) Bray, K. L.; Fairlamb, I. J. S.; Lloyd-Jones, G. C. Chem. Commun 2001, 187-188; (p) Kisanga, P.; Goj, L. A.; Widenhoefer, R. A. J. Org. Chem. 2001, 66, 635-637; (q) Oh, C. H.; Kim, J. D.; Han, J. W. Chem. Lett. 2001, 1290-1291; (r) Goj, L. A.; Widenhoefer, R. A. J. Am. Chem. Soc. 2001, 123, 11133-11147.
12. For leading papers in the last decade, see: Ti: (a) Thorn, M. G.; Hill, J. E.; Waratuke, S. A.; Johnson, E. S.; Franwick, P. E.; Rothwell, I. P. J. Am. Chem. Soc. 1997, 119, 8630-8641; (b) Okamoto, S.; Livinghouse, T. J. Am. Chem. Soc. 2000, 122, 1223-1224; (c) Okamoto, S.; Livinghouse, T. Organometallics 2000, 19, 1449-1451. Zr: (d) Christoffers, J.; Bergman, R. G. J. Am. Chem. Soc. 1996, 118, 4715-4716; (e) Thiele, S.; Erker, G. Ber./Recl. 1997, 130, 201-207; (f) Bazan, G. C.; Rodriguez, G.; Ashe, A. J., III; Al-Ahmad, S.; Kampf, J. W. Organometallics 1997, 16, 2492-2494; (g) Schweder, B.; Walther, D.; Döhler, T.; Klobes, O.; Görls, H. J. Prakt. Chem. 1999, 341, 736-747. Ru: (h) Yamamoto, Y.; Ohkoshi, N.; Itoh, K. J. Org. Chem. 1999, 64, 2178-2179; (i) Yamamoto, Y.; Nakagai, Y.; Ohkoshi, N.; Itoh, K. J. Am. Chem. Soc. 2001, 123, 6372-6380. Ni: (j) Radetich, B.; RajanBabu, T. V. J. Am. Chem. Soc. 1998, 120, 8007-8008; (k) Walther, D.; Döhler, T.; Heubach, K.; Klobes, O.; Schweder, B.; Görls, H. Z. Anorg. Allg. Chem. 1999, 625, 923-932. Pd: (l) Heumann, A.; Moukhliss, M. Synlett 1998, 1211-1212; (m) Widenhoefer, R. A.; Perch, N. S. Org. Lett. 1999, 1, 1103-1105; (n) Kisanga, P.; Widenhoefer, R. A. J. Am. Chem. Soc. 2000, 122, 10017-10026; (o) Bray, K. L.; Fairlamb, I. J. S.; Lloyd-Jones, G. C. Chem. Commun 2001, 187-188; (p) Kisanga, P.; Goj, L. A.; Widenhoefer, R. A. J. Org. Chem. 2001, 66, 635-637; (q) Oh, C. H.; Kim, J. D.; Han, J. W. Chem. Lett. 2001, 1290-1291; (r) Goj, L. A.; Widenhoefer, R. A. J. Am. Chem. Soc. 2001, 123, 11133-11147.
13. For leading papers in the last decade, see: Ti: (a) Thorn, M. G.; Hill, J. E.; Waratuke, S. A.; Johnson, E. S.; Franwick, P. E.; Rothwell, I. P. J. Am. Chem. Soc. 1997, 119, 8630-8641; (b) Okamoto, S.; Livinghouse, T. J. Am. Chem. Soc. 2000, 122, 1223-1224; (c) Okamoto, S.; Livinghouse, T. Organometallics 2000, 19, 1449-1451. Zr: (d) Christoffers, J.; Bergman, R. G. J. Am. Chem. Soc. 1996, 118, 4715-4716; (e) Thiele, S.; Erker, G. Ber./Recl. 1997, 130, 201-207; (f) Bazan, G. C.; Rodriguez, G.; Ashe, A. J., III; Al-Ahmad, S.; Kampf, J. W. Organometallics 1997, 16, 2492-2494; (g) Schweder, B.; Walther, D.; Döhler, T.; Klobes, O.; Görls, H. J. Prakt. Chem. 1999, 341, 736-747. Ru: (h) Yamamoto, Y.; Ohkoshi, N.; Itoh, K. J. Org. Chem. 1999, 64, 2178-2179; (i) Yamamoto, Y.; Nakagai, Y.; Ohkoshi, N.; Itoh, K. J. Am. Chem. Soc. 2001, 123, 6372-6380. Ni: (j) Radetich, B.; RajanBabu, T. V. J. Am. Chem. Soc. 1998, 120, 8007-8008; (k) Walther, D.; Döhler, T.; Heubach, K.; Klobes, O.; Schweder, B.; Görls, H. Z. Anorg. Allg. Chem. 1999, 625, 923-932. Pd: (l) Heumann, A.; Moukhliss, M. Synlett 1998, 1211-1212; (m) Widenhoefer, R. A.; Perch, N. S. Org. Lett. 1999, 1, 1103-1105; (n) Kisanga, P.; Widenhoefer, R. A. J. Am. Chem. Soc. 2000, 122, 10017-10026; (o) Bray, K. L.; Fairlamb, I. J. S.; Lloyd-Jones, G. C. Chem. Commun 2001, 187-188; (p) Kisanga, P.; Goj, L. A.; Widenhoefer, R. A. J. Org. Chem. 2001, 66, 635-637; (q) Oh, C. H.; Kim, J. D.; Han, J. W. Chem. Lett. 2001, 1290-1291; (r) Goj, L. A.; Widenhoefer, R. A. J. Am. Chem. Soc. 2001, 123, 11133-11147.
14. For leading papers in the last decade, see: Ti: (a) Thorn, M. G.; Hill, J. E.; Waratuke, S. A.; Johnson, E. S.; Franwick, P. E.; Rothwell, I. P. J. Am. Chem. Soc. 1997, 119, 8630-8641; (b) Okamoto, S.; Livinghouse, T. J. Am. Chem. Soc. 2000, 122, 1223-1224; (c) Okamoto, S.; Livinghouse, T. Organometallics 2000, 19, 1449-1451. Zr: (d) Christoffers, J.; Bergman, R. G. J. Am. Chem. Soc. 1996, 118, 4715-4716; (e) Thiele, S.; Erker, G. Ber./Recl. 1997, 130, 201-207; (f) Bazan, G. C.; Rodriguez, G.; Ashe, A. J., III; Al-Ahmad, S.; Kampf, J. W. Organometallics 1997, 16, 2492-2494; (g) Schweder, B.; Walther, D.; Döhler, T.; Klobes, O.; Görls, H. J. Prakt. Chem. 1999, 341, 736-747. Ru: (h) Yamamoto, Y.; Ohkoshi, N.; Itoh, K. J. Org. Chem. 1999, 64, 2178-2179; (i) Yamamoto, Y.; Nakagai, Y.; Ohkoshi, N.; Itoh, K. J. Am. Chem. Soc. 2001, 123, 6372-6380. Ni: (j) Radetich, B.; RajanBabu, T. V. J. Am. Chem. Soc. 1998, 120, 8007-8008; (k) Walther, D.; Döhler, T.; Heubach, K.; Klobes, O.; Schweder, B.; Görls, H. Z. Anorg. Allg. Chem. 1999, 625, 923-932. Pd: (l) Heumann, A.; Moukhliss, M. Synlett 1998, 1211-1212; (m) Widenhoefer, R. A.; Perch, N. S. Org. Lett. 1999, 1, 1103-1105; (n) Kisanga, P.; Widenhoefer, R. A. J. Am. Chem. Soc. 2000, 122, 10017-10026; (o) Bray, K. L.; Fairlamb, I. J. S.; Lloyd-Jones, G. C. Chem. Commun 2001, 187-188; (p) Kisanga, P.; Goj, L. A.; Widenhoefer, R. A. J. Org. Chem. 2001, 66, 635-637; (q) Oh, C. H.; Kim, J. D.; Han, J. W. Chem. Lett. 2001, 1290-1291; (r) Goj, L. A.; Widenhoefer, R. A. J. Am. Chem. Soc. 2001, 123, 11133-11147.
15. For leading papers in the last decade, see: Ti: (a) Thorn, M. G.; Hill, J. E.; Waratuke, S. A.; Johnson, E. S.; Franwick, P. E.; Rothwell, I. P. J. Am. Chem. Soc. 1997, 119, 8630-8641; (b) Okamoto, S.; Livinghouse, T. J. Am. Chem. Soc. 2000, 122, 1223-1224; (c) Okamoto, S.; Livinghouse, T. Organometallics 2000, 19, 1449-1451. Zr: (d) Christoffers, J.; Bergman, R. G. J. Am. Chem. Soc. 1996, 118, 4715-4716; (e) Thiele, S.; Erker, G. Ber./Recl. 1997, 130, 201-207; (f) Bazan, G. C.; Rodriguez, G.; Ashe, A. J., III; Al-Ahmad, S.; Kampf, J. W. Organometallics 1997, 16, 2492-2494; (g) Schweder, B.; Walther, D.; Döhler, T.; Klobes, O.; Görls, H. J. Prakt. Chem. 1999, 341, 736-747. Ru: (h) Yamamoto, Y.; Ohkoshi, N.; Itoh, K. J. Org. Chem. 1999, 64, 2178-2179; (i) Yamamoto, Y.; Nakagai, Y.; Ohkoshi, N.; Itoh, K. J. Am. Chem. Soc. 2001, 123, 6372-6380. Ni: (j) Radetich, B.; RajanBabu, T. V. J. Am. Chem. Soc. 1998, 120, 8007-8008; (k) Walther, D.; Döhler, T.; Heubach, K.; Klobes, O.; Schweder, B.; Görls, H. Z. Anorg. Allg. Chem. 1999, 625, 923-932. Pd: (l) Heumann, A.; Moukhliss, M. Synlett 1998, 1211-1212; (m) Widenhoefer, R. A.; Perch, N. S. Org. Lett. 1999, 1, 1103-1105; (n) Kisanga, P.; Widenhoefer, R. A. J. Am. Chem. Soc. 2000, 122, 10017-10026; (o) Bray, K. L.; Fairlamb, I. J. S.; Lloyd-Jones, G. C. Chem. Commun 2001, 187-188; (p) Kisanga, P.; Goj, L. A.; Widenhoefer, R. A. J. Org. Chem. 2001, 66, 635-637; (q) Oh, C. H.; Kim, J. D.; Han, J. W. Chem. Lett. 2001, 1290-1291; (r) Goj, L. A.; Widenhoefer, R. A. J. Am. Chem. Soc. 2001, 123, 11133-11147.
16. For leading papers in the last decade, see: Ti: (a) Thorn, M. G.; Hill, J. E.; Waratuke, S. A.; Johnson, E. S.; Franwick, P. E.; Rothwell, I. P. J. Am. Chem. Soc. 1997, 119, 8630-8641; (b) Okamoto, S.; Livinghouse, T. J. Am. Chem. Soc. 2000, 122, 1223-1224; (c) Okamoto, S.; Livinghouse, T. Organometallics 2000, 19, 1449-1451. Zr: (d) Christoffers, J.; Bergman, R. G. J. Am. Chem. Soc. 1996, 118, 4715-4716; (e) Thiele, S.; Erker, G. Ber./Recl. 1997, 130, 201-207; (f) Bazan, G. C.; Rodriguez, G.; Ashe, A. J., III; Al-Ahmad, S.; Kampf, J. W. Organometallics 1997, 16, 2492-2494; (g) Schweder, B.; Walther, D.; Döhler, T.; Klobes, O.; Görls, H. J. Prakt. Chem. 1999, 341, 736-747. Ru: (h) Yamamoto, Y.; Ohkoshi, N.; Itoh, K. J. Org. Chem. 1999, 64, 2178-2179; (i) Yamamoto, Y.; Nakagai, Y.; Ohkoshi, N.; Itoh, K. J. Am. Chem. Soc. 2001, 123, 6372-6380. Ni: (j) Radetich, B.; RajanBabu, T. V. J. Am. Chem. Soc. 1998, 120, 8007-8008; (k) Walther, D.; Döhler, T.; Heubach, K.; Klobes, O.; Schweder, B.; Görls, H. Z. Anorg. Allg. Chem. 1999, 625, 923-932. Pd: (l) Heumann, A.; Moukhliss, M. Synlett 1998, 1211-1212; (m) Widenhoefer, R. A.; Perch, N. S. Org. Lett. 1999, 1, 1103-1105; (n) Kisanga, P.; Widenhoefer, R. A. J. Am. Chem. Soc. 2000, 122, 10017-10026; (o) Bray, K. L.; Fairlamb, I. J. S.; Lloyd-Jones, G. C. Chem. Commun 2001, 187-188; (p) Kisanga, P.; Goj, L. A.; Widenhoefer, R. A. J. Org. Chem. 2001, 66, 635-637; (q) Oh, C. H.; Kim, J. D.; Han, J. W. Chem. Lett. 2001, 1290-1291; (r) Goj, L. A.; Widenhoefer, R. A. J. Am. Chem. Soc. 2001, 123, 11133-11147.
17. For leading papers in the last decade, see: Ti: (a) Thorn, M. G.; Hill, J. E.; Waratuke, S. A.; Johnson, E. S.; Franwick, P. E.; Rothwell, I. P. J. Am. Chem. Soc. 1997, 119, 8630-8641; (b) Okamoto, S.; Livinghouse, T. J. Am. Chem. Soc. 2000, 122, 1223-1224; (c) Okamoto, S.; Livinghouse, T. Organometallics 2000, 19, 1449-1451. Zr: (d) Christoffers, J.; Bergman, R. G. J. Am. Chem. Soc. 1996, 118, 4715-4716; (e) Thiele, S.; Erker, G. Ber./Recl. 1997, 130, 201-207; (f) Bazan, G. C.; Rodriguez, G.; Ashe, A. J., III; Al-Ahmad, S.; Kampf, J. W. Organometallics 1997, 16, 2492-2494; (g) Schweder, B.; Walther, D.; Döhler, T.; Klobes, O.; Görls, H. J. Prakt. Chem. 1999, 341, 736-747. Ru: (h) Yamamoto, Y.; Ohkoshi, N.; Itoh, K. J. Org. Chem. 1999, 64, 2178-2179; (i) Yamamoto, Y.; Nakagai, Y.; Ohkoshi, N.; Itoh, K. J. Am. Chem. Soc. 2001, 123, 6372-6380. Ni: (j) Radetich, B.; RajanBabu, T. V. J. Am. Chem. Soc. 1998, 120, 8007-8008; (k) Walther, D.; Döhler, T.; Heubach, K.; Klobes, O.; Schweder, B.; Görls, H. Z. Anorg. Allg. Chem. 1999, 625, 923-932. Pd: (l) Heumann, A.; Moukhliss, M. Synlett 1998, 1211-1212; (m) Widenhoefer, R. A.; Perch, N. S. Org. Lett. 1999, 1, 1103-1105; (n) Kisanga, P.; Widenhoefer, R. A. J. Am. Chem. Soc. 2000, 122, 10017-10026; (o) Bray, K. L.; Fairlamb, I. J. S.; Lloyd-Jones, G. C. Chem. Commun 2001, 187-188; (p) Kisanga, P.; Goj, L. A.; Widenhoefer, R. A. J. Org. Chem. 2001, 66, 635-637; (q) Oh, C. H.; Kim, J. D.; Han, J. W. Chem. Lett. 2001, 1290-1291; (r) Goj, L. A.; Widenhoefer, R. A. J. Am. Chem. Soc. 2001, 123, 11133-11147.
18. For leading papers in the last decade, see: Ti: (a) Thorn, M. G.; Hill, J. E.; Waratuke, S. A.; Johnson, E. S.; Franwick, P. E.; Rothwell, I. P. J. Am. Chem. Soc. 1997, 119, 8630-8641; (b) Okamoto, S.; Livinghouse, T. J. Am. Chem. Soc. 2000, 122, 1223-1224; (c) Okamoto, S.; Livinghouse, T. Organometallics 2000, 19, 1449-1451. Zr: (d) Christoffers, J.; Bergman, R. G. J. Am. Chem. Soc. 1996, 118, 4715-4716; (e) Thiele, S.; Erker, G. Ber./Recl. 1997, 130, 201-207; (f) Bazan, G. C.; Rodriguez, G.; Ashe, A. J., III; Al-Ahmad, S.; Kampf, J. W. Organometallics 1997, 16, 2492-2494; (g) Schweder, B.; Walther, D.; Döhler, T.; Klobes, O.; Görls, H. J. Prakt. Chem. 1999, 341, 736-747. Ru: (h) Yamamoto, Y.; Ohkoshi, N.; Itoh, K. J. Org. Chem. 1999, 64, 2178-2179; (i) Yamamoto, Y.; Nakagai, Y.; Ohkoshi, N.; Itoh, K. J. Am. Chem. Soc. 2001, 123, 6372-6380. Ni: (j) Radetich, B.; RajanBabu, T. V. J. Am. Chem. Soc. 1998, 120, 8007-8008; (k) Walther, D.; Döhler, T.; Heubach, K.; Klobes, O.; Schweder, B.; Görls, H. Z. Anorg. Allg. Chem. 1999, 625, 923-932. Pd: (l) Heumann, A.; Moukhliss, M. Synlett 1998, 1211-1212; (m) Widenhoefer, R. A.; Perch, N. S. Org. Lett. 1999, 1, 1103-1105; (n) Kisanga, P.; Widenhoefer, R. A. J. Am. Chem. Soc. 2000, 122, 10017-10026; (o) Bray, K. L.; Fairlamb, I. J. S.; Lloyd-Jones, G. C. Chem. Commun 2001, 187-188; (p) Kisanga, P.; Goj, L. A.; Widenhoefer, R. A. J. Org. Chem. 2001, 66, 635-637; (q) Oh, C. H.; Kim, J. D.; Han, J. W. Chem. Lett. 2001, 1290-1291; (r) Goj, L. A.; Widenhoefer, R. A. J. Am. Chem. Soc. 2001, 123, 11133-11147.
19. For leading papers in the last decade, see: Ti: (a) Thorn, M. G.; Hill, J. E.; Waratuke, S. A.; Johnson, E. S.; Franwick, P. E.; Rothwell, I. P. J. Am. Chem. Soc. 1997, 119, 8630-8641; (b) Okamoto, S.; Livinghouse, T. J. Am. Chem. Soc. 2000, 122, 1223-1224; (c) Okamoto, S.; Livinghouse, T. Organometallics 2000, 19, 1449-1451. Zr: (d) Christoffers, J.; Bergman, R. G. J. Am. Chem. Soc. 1996, 118, 4715-4716; (e) Thiele, S.; Erker, G. Ber./Recl. 1997, 130, 201-207; (f) Bazan, G. C.; Rodriguez, G.; Ashe, A. J., III; Al-Ahmad, S.; Kampf, J. W. Organometallics 1997, 16, 2492-2494; (g) Schweder, B.; Walther, D.; Döhler, T.; Klobes, O.; Görls, H. J. Prakt. Chem. 1999, 341, 736-747. Ru: (h) Yamamoto, Y.; Ohkoshi, N.; Itoh, K. J. Org. Chem. 1999, 64, 2178-2179; (i) Yamamoto, Y.; Nakagai, Y.; Ohkoshi, N.; Itoh, K. J. Am. Chem. Soc. 2001, 123, 6372-6380. Ni: (j) Radetich, B.; RajanBabu, T. V. J. Am. Chem. Soc. 1998, 120, 8007-8008; (k) Walther, D.; Döhler, T.; Heubach, K.; Klobes, O.; Schweder, B.; Görls, H. Z. Anorg. Allg. Chem. 1999, 625, 923-932. Pd: (l) Heumann, A.; Moukhliss, M. Synlett 1998, 1211-1212; (m) Widenhoefer, R. A.; Perch, N. S. Org. Lett. 1999, 1, 1103-1105; (n) Kisanga, P.; Widenhoefer, R. A. J. Am. Chem. Soc. 2000, 122, 10017-10026; (o) Bray, K. L.; Fairlamb, I. J. S.; Lloyd-Jones, G. C. Chem. Commun 2001, 187-188; (p) Kisanga, P.; Goj, L. A.; Widenhoefer, R. A. J. Org. Chem. 2001, 66, 635-637; (q) Oh, C. H.; Kim, J. D.; Han, J. W. Chem. Lett. 2001, 1290-1291; (r) Goj, L. A.; Widenhoefer, R. A. J. Am. Chem. Soc. 2001, 123, 11133-11147.
20. For leading papers in the last decade, see: Ti: (a) Thorn, M. G.; Hill, J. E.; Waratuke, S. A.; Johnson, E. S.; Franwick, P. E.; Rothwell, I. P. J. Am. Chem. Soc. 1997, 119, 8630-8641; (b) Okamoto, S.; Livinghouse, T. J. Am. Chem. Soc. 2000, 122, 1223-1224; (c) Okamoto, S.; Livinghouse, T. Organometallics 2000, 19, 1449-1451. Zr: (d) Christoffers, J.; Bergman, R. G. J. Am. Chem. Soc. 1996, 118, 4715-4716; (e) Thiele, S.; Erker, G. Ber./Recl. 1997, 130, 201-207; (f) Bazan, G. C.; Rodriguez, G.; Ashe, A. J., III; Al-Ahmad, S.; Kampf, J. W. Organometallics 1997, 16, 2492-2494; (g) Schweder, B.; Walther, D.; Döhler, T.; Klobes, O.; Görls, H. J. Prakt. Chem. 1999, 341, 736-747. Ru: (h) Yamamoto, Y.; Ohkoshi, N.; Itoh, K. J. Org. Chem. 1999, 64, 2178-2179; (i) Yamamoto, Y.; Nakagai, Y.; Ohkoshi, N.; Itoh, K. J. Am. Chem. Soc. 2001, 123, 6372-6380. Ni: (j) Radetich, B.; RajanBabu, T. V. J. Am. Chem. Soc. 1998, 120, 8007-8008; (k) Walther, D.; Döhler, T.; Heubach, K.; Klobes, O.; Schweder, B.; Görls, H. Z. Anorg. Allg. Chem. 1999, 625, 923-932. Pd: (l) Heumann, A.; Moukhliss, M. Synlett 1998, 1211-1212; (m) Widenhoefer, R. A.; Perch, N. S. Org. Lett. 1999, 1, 1103-1105; (n) Kisanga, P.; Widenhoefer, R. A. J. Am. Chem. Soc. 2000, 122, 10017-10026; (o) Bray, K. L.; Fairlamb, I. J. S.; Lloyd-Jones, G. C. Chem. Commun 2001, 187-188; (p) Kisanga, P.; Goj, L. A.; Widenhoefer, R. A. J. Org. Chem. 2001, 66, 635-637; (q) Oh, C. H.; Kim, J. D.; Han, J. W. Chem. Lett. 2001, 1290-1291; (r) Goj, L. A.; Widenhoefer, R. A. J. Am. Chem. Soc. 2001, 123, 11133-11147.
21. For leading papers in the last decade, see: Ti: (a) Thorn, M. G.; Hill, J. E.; Waratuke, S. A.; Johnson, E. S.; Franwick, P. E.; Rothwell, I. P. J. Am. Chem. Soc. 1997, 119, 8630-8641; (b) Okamoto, S.; Livinghouse, T. J. Am. Chem. Soc. 2000, 122, 1223-1224; (c) Okamoto, S.; Livinghouse, T. Organometallics 2000, 19, 1449-1451. Zr: (d) Christoffers, J.; Bergman, R. G. J. Am. Chem. Soc. 1996, 118, 4715-4716; (e) Thiele, S.; Erker, G. Ber./Recl. 1997, 130, 201-207; (f) Bazan, G. C.; Rodriguez, G.; Ashe, A. J., III; Al-Ahmad, S.; Kampf, J. W. Organometallics 1997, 16, 2492-2494; (g) Schweder, B.; Walther, D.; Döhler, T.; Klobes, O.; Görls, H. J. Prakt. Chem. 1999, 341, 736-747. Ru: (h) Yamamoto, Y.; Ohkoshi, N.; Itoh, K. J. Org. Chem. 1999, 64, 2178-2179; (i) Yamamoto, Y.; Nakagai, Y.; Ohkoshi, N.; Itoh, K. J. Am. Chem. Soc. 2001, 123, 6372-6380. Ni: (j) Radetich, B.; RajanBabu, T. V. J. Am. Chem. Soc. 1998, 120, 8007-8008; (k) Walther, D.; Döhler, T.; Heubach, K.; Klobes, O.; Schweder, B.; Görls, H. Z. Anorg. Allg. Chem. 1999, 625, 923-932. Pd: (l) Heumann, A.; Moukhliss, M. Synlett 1998, 1211-1212; (m) Widenhoefer, R. A.; Perch, N. S. Org. Lett. 1999, 1, 1103-1105; (n) Kisanga, P.; Widenhoefer, R. A. J. Am. Chem. Soc. 2000, 122, 10017-10026; (o) Bray, K. L.; Fairlamb, I. J. S.; Lloyd-Jones, G. C. Chem. Commun 2001, 187-188; (p) Kisanga, P.; Goj, L. A.; Widenhoefer, R. A. J. Org. Chem. 2001, 66, 635-637; (q) Oh, C. H.; Kim, J. D.; Han, J. W. Chem. Lett. 2001, 1290-1291; (r) Goj, L. A.; Widenhoefer, R. A. J. Am. Chem. Soc. 2001, 123, 11133-11147.
22. For leading papers in the last decade, see: Ti: (a) Thorn, M. G.; Hill, J. E.; Waratuke, S. A.; Johnson, E. S.; Franwick, P. E.; Rothwell, I. P. J. Am. Chem. Soc. 1997, 119, 8630-8641; (b) Okamoto, S.; Livinghouse, T. J. Am. Chem. Soc. 2000, 122, 1223-1224; (c) Okamoto, S.; Livinghouse, T. Organometallics 2000, 19, 1449-1451. Zr: (d) Christoffers, J.; Bergman, R. G. J. Am. Chem. Soc. 1996, 118, 4715-4716; (e) Thiele, S.; Erker, G. Ber./Recl. 1997, 130, 201-207; (f) Bazan, G. C.; Rodriguez, G.; Ashe, A. J., III; Al-Ahmad, S.; Kampf, J. W. Organometallics 1997, 16, 2492-2494; (g) Schweder, B.; Walther, D.; Döhler, T.; Klobes, O.; Görls, H. J. Prakt. Chem. 1999, 341, 736-747. Ru: (h) Yamamoto, Y.; Ohkoshi, N.; Itoh, K. J. Org. Chem. 1999, 64, 2178-2179; (i) Yamamoto, Y.; Nakagai, Y.; Ohkoshi, N.; Itoh, K. J. Am. Chem. Soc. 2001, 123, 6372-6380. Ni: (j) Radetich, B.; RajanBabu, T. V. J. Am. Chem. Soc. 1998, 120, 8007-8008; (k) Walther, D.; Döhler, T.; Heubach, K.; Klobes, O.; Schweder, B.; Görls, H. Z. Anorg. Allg. Chem. 1999, 625, 923-932. Pd: (l) Heumann, A.; Moukhliss, M. Synlett 1998, 1211-1212; (m) Widenhoefer, R. A.; Perch, N. S. Org. Lett. 1999, 1, 1103-1105; (n) Kisanga, P.; Widenhoefer, R. A. J. Am. Chem. Soc. 2000, 122, 10017-10026; (o) Bray, K. L.; Fairlamb, I. J. S.; Lloyd-Jones, G. C. Chem. Commun 2001, 187-188; (p) Kisanga, P.; Goj, L. A.; Widenhoefer, R. A. J. Org. Chem. 2001, 66, 635-637; (q) Oh, C. H.; Kim, J. D.; Han, J. W. Chem. Lett. 2001, 1290-1291; (r) Goj, L. A.; Widenhoefer, R. A. J. Am. Chem. Soc. 2001, 123, 11133-11147.
23. For leading papers in the last decade, see: Ti: (a) Thorn, M. G.; Hill, J. E.; Waratuke, S. A.; Johnson, E. S.; Franwick, P. E.; Rothwell, I. P. J. Am. Chem. Soc. 1997, 119, 8630-8641; (b) Okamoto, S.; Livinghouse, T. J. Am. Chem. Soc. 2000, 122, 1223-1224; (c) Okamoto, S.; Livinghouse, T. Organometallics 2000, 19, 1449-1451. Zr: (d) Christoffers, J.; Bergman, R. G. J. Am. Chem. Soc. 1996, 118, 4715-4716; (e) Thiele, S.; Erker, G. Ber./Recl. 1997, 130, 201-207; (f) Bazan, G. C.; Rodriguez, G.; Ashe, A. J., III; Al-Ahmad, S.; Kampf, J. W. Organometallics 1997, 16, 2492-2494; (g) Schweder, B.; Walther, D.; Döhler, T.; Klobes, O.; Görls, H. J. Prakt. Chem. 1999, 341, 736-747. Ru: (h) Yamamoto, Y.; Ohkoshi, N.; Itoh, K. J. Org. Chem. 1999, 64, 2178-2179; (i) Yamamoto, Y.; Nakagai, Y.; Ohkoshi, N.; Itoh, K. J. Am. Chem. Soc. 2001, 123, 6372-6380. Ni: (j) Radetich, B.; RajanBabu, T. V. J. Am. Chem. Soc. 1998, 120, 8007-8008; (k) Walther, D.; Döhler, T.; Heubach, K.; Klobes, O.; Schweder, B.; Görls, H. Z. Anorg. Allg. Chem. 1999, 625, 923-932. Pd: (l) Heumann, A.; Moukhliss, M. Synlett 1998, 1211-1212; (m) Widenhoefer, R. A.; Perch, N. S. Org. Lett. 1999, 1, 1103-1105; (n) Kisanga, P.; Widenhoefer, R. A. J. Am. Chem. Soc. 2000, 122, 10017-10026; (o) Bray, K. L.; Fairlamb, I. J. S.; Lloyd-Jones, G. C. Chem. Commun 2001, 187-188; (p) Kisanga, P.; Goj, L. A.; Widenhoefer, R. A. J. Org. Chem. 2001, 66, 635-637; (q) Oh, C. H.; Kim, J. D.; Han, J. W. Chem. Lett. 2001, 1290-1291; (r) Goj, L. A.; Widenhoefer, R. A. J. Am. Chem. Soc. 2001, 123, 11133-11147.
24. For leading papers in the last decade, see: Ti: (a) Thorn, M. G.; Hill, J. E.; Waratuke, S. A.; Johnson, E. S.; Franwick, P. E.; Rothwell, I. P. J. Am. Chem. Soc. 1997, 119, 8630-8641; (b) Okamoto, S.; Livinghouse, T. J. Am. Chem. Soc. 2000, 122, 1223-1224; (c) Okamoto, S.; Livinghouse, T. Organometallics 2000, 19, 1449-1451. Zr: (d) Christoffers, J.; Bergman, R. G. J. Am. Chem. Soc. 1996, 118, 4715-4716; (e) Thiele, S.; Erker, G. Ber./Recl. 1997, 130, 201-207; (f) Bazan, G. C.; Rodriguez, G.; Ashe, A. J., III; Al-Ahmad, S.; Kampf, J. W. Organometallics 1997, 16, 2492-2494; (g) Schweder, B.; Walther, D.; Döhler, T.; Klobes, O.; Görls, H. J. Prakt. Chem. 1999, 341, 736-747. Ru: (h) Yamamoto, Y.; Ohkoshi, N.; Itoh, K. J. Org. Chem. 1999, 64, 2178-2179; (i) Yamamoto, Y.; Nakagai, Y.; Ohkoshi, N.; Itoh, K. J. Am. Chem. Soc. 2001, 123, 6372-6380. Ni: (j) Radetich, B.; RajanBabu, T. V. J. Am. Chem. Soc. 1998, 120, 8007-8008; (k) Walther, D.; Döhler, T.; Heubach, K.; Klobes, O.; Schweder, B.; Görls, H. Z. Anorg. Allg. Chem. 1999, 625, 923-932. Pd: (l) Heumann, A.; Moukhliss, M. Synlett 1998, 1211-1212; (m) Widenhoefer, R. A.; Perch, N. S. Org. Lett. 1999, 1, 1103-1105; (n) Kisanga, P.; Widenhoefer, R. A. J. Am. Chem. Soc. 2000, 122, 10017-10026; (o) Bray, K. L.; Fairlamb, I. J. S.; Lloyd-Jones, G. C. Chem. Commun 2001, 187-188; (p) Kisanga, P.; Goj, L. A.; Widenhoefer, R. A. J. Org. Chem. 2001, 66, 635-637; (q) Oh, C. H.; Kim, J. D.; Han, J. W. Chem. Lett. 2001, 1290-1291; (r) Goj, L. A.; Widenhoefer, R. A. J. Am. Chem. Soc. 2001, 123, 11133-11147.
25. For leading papers in the last decade, see: Ti: (a) Thorn, M. G.; Hill, J. E.; Waratuke, S. A.; Johnson, E. S.; Franwick, P. E.; Rothwell, I. P. J. Am. Chem. Soc. 1997, 119, 8630-8641; (b) Okamoto, S.; Livinghouse, T. J. Am. Chem. Soc. 2000, 122, 1223-1224; (c) Okamoto, S.; Livinghouse, T. Organometallics 2000, 19, 1449-1451. Zr: (d) Christoffers, J.; Bergman, R. G. J. Am. Chem. Soc. 1996, 118, 4715-4716; (e) Thiele, S.; Erker, G. Ber./Recl. 1997, 130, 201-207; (f) Bazan, G. C.; Rodriguez, G.; Ashe, A. J., III; Al-Ahmad, S.; Kampf, J. W. Organometallics 1997, 16, 2492-2494; (g) Schweder, B.; Walther, D.; Döhler, T.; Klobes, O.; Görls, H. J. Prakt. Chem. 1999, 341, 736-747. Ru: (h) Yamamoto, Y.; Ohkoshi, N.; Itoh, K. J. Org. Chem. 1999, 64, 2178-2179; (i) Yamamoto, Y.; Nakagai, Y.; Ohkoshi, N.; Itoh, K. J. Am. Chem. Soc. 2001, 123, 6372-6380. Ni: (j) Radetich, B.; RajanBabu, T. V. J. Am. Chem. Soc. 1998, 120, 8007-8008; (k) Walther, D.; Döhler, T.; Heubach, K.; Klobes, O.; Schweder, B.; Görls, H. Z. Anorg. Allg. Chem. 1999, 625, 923-932. Pd: (l) Heumann, A.; Moukhliss, M. Synlett 1998, 1211-1212; (m) Widenhoefer, R. A.; Perch, N. S. Org. Lett. 1999, 1, 1103-1105; (n) Kisanga, P.; Widenhoefer, R. A. J. Am. Chem. Soc. 2000, 122, 10017-10026; (o) Bray, K. L.; Fairlamb, I. J. S.; Lloyd-Jones, G. C. Chem. Commun 2001, 187-188; (p) Kisanga, P.; Goj, L. A.; Widenhoefer, R. A. J. Org. Chem. 2001, 66, 635-637; (q) Oh, C. H.; Kim, J. D.; Han, J. W. Chem. Lett. 2001, 1290-1291; (r) Goj, L. A.; Widenhoefer, R. A. J. Am. Chem. Soc. 2001, 123, 11133-11147.
26. For leading papers in the last decade, see: Ti: (a) Thorn, M. G.; Hill, J. E.; Waratuke, S. A.; Johnson, E. S.; Franwick, P. E.; Rothwell, I. P. J. Am. Chem. Soc. 1997, 119, 8630-8641; (b) Okamoto, S.; Livinghouse, T. J. Am. Chem. Soc. 2000, 122, 1223-1224; (c) Okamoto, S.; Livinghouse, T. Organometallics 2000, 19, 1449-1451. Zr: (d) Christoffers, J.; Bergman, R. G. J. Am. Chem. Soc. 1996, 118, 4715-4716; (e) Thiele, S.; Erker, G. Ber./Recl. 1997, 130, 201-207; (f) Bazan, G. C.; Rodriguez, G.; Ashe, A. J., III; Al-Ahmad, S.; Kampf, J. W. Organometallics 1997, 16, 2492-2494; (g) Schweder, B.; Walther, D.; Döhler, T.; Klobes, O.; Görls, H. J. Prakt. Chem. 1999, 341, 736-747. Ru: (h) Yamamoto, Y.; Ohkoshi, N.; Itoh, K. J. Org. Chem. 1999, 64, 2178-2179; (i) Yamamoto, Y.; Nakagai, Y.; Ohkoshi, N.; Itoh, K. J. Am. Chem. Soc. 2001, 123, 6372-6380. Ni: (j) Radetich, B.; RajanBabu, T. V. J. Am. Chem. Soc. 1998, 120, 8007-8008; (k) Walther, D.; Döhler, T.; Heubach, K.; Klobes, O.; Schweder, B.; Görls, H. Z. Anorg. Allg. Chem. 1999, 625, 923-932. Pd: (l) Heumann, A.; Moukhliss, M. Synlett 1998, 1211-1212; (m) Widenhoefer, R. A.; Perch, N. S. Org. Lett. 1999, 1, 1103-1105; (n) Kisanga, P.; Widenhoefer, R. A. J. Am. Chem. Soc. 2000, 122, 10017-10026; (o) Bray, K. L.; Fairlamb, I. J. S.; Lloyd-Jones, G. C. Chem. Commun 2001, 187-188; (p) Kisanga, P.; Goj, L. A.; Widenhoefer, R. A. J. Org. Chem. 2001, 66, 635-637; (q) Oh, C. H.; Kim, J. D.; Han, J. W. Chem. Lett. 2001, 1290-1291; (r) Goj, L. A.; Widenhoefer, R. A. J. Am. Chem. Soc. 2001, 123, 11133-11147.
27. For leading papers in the last decade, see: Ti: (a) Thorn, M. G.; Hill, J. E.; Waratuke, S. A.; Johnson, E. S.; Franwick, P. E.; Rothwell, I. P. J. Am. Chem. Soc. 1997, 119, 8630-8641; (b) Okamoto, S.; Livinghouse, T. J. Am. Chem. Soc. 2000, 122, 1223-1224; (c) Okamoto, S.; Livinghouse, T. Organometallics 2000, 19, 1449-1451. Zr: (d) Christoffers, J.; Bergman, R. G. J. Am. Chem. Soc. 1996, 118, 4715-4716; (e) Thiele, S.; Erker, G. Ber./Recl. 1997, 130, 201-207; (f) Bazan, G. C.; Rodriguez, G.; Ashe, A. J., III; Al-Ahmad, S.; Kampf, J. W. Organometallics 1997, 16, 2492-2494; (g) Schweder, B.; Walther, D.; Döhler, T.; Klobes, O.; Görls, H. J. Prakt. Chem. 1999, 341, 736-747. Ru: (h) Yamamoto, Y.; Ohkoshi, N.; Itoh, K. J. Org. Chem. 1999, 64, 2178-2179; (i) Yamamoto, Y.; Nakagai, Y.; Ohkoshi, N.; Itoh, K. J. Am. Chem. Soc. 2001, 123, 6372-6380. Ni: (j) Radetich, B.; RajanBabu, T. V. J. Am. Chem. Soc. 1998, 120, 8007-8008; (k) Walther, D.; Döhler, T.; Heubach, K.; Klobes, O.; Schweder, B.; Görls, H. Z. Anorg. Allg. Chem. 1999, 625, 923-932. Pd: (l) Heumann, A.; Moukhliss, M. Synlett 1998, 1211-1212; (m) Widenhoefer, R. A.; Perch, N. S. Org. Lett. 1999, 1, 1103-1105; (n) Kisanga, P.; Widenhoefer, R. A. J. Am. Chem. Soc. 2000, 122, 10017-10026; (o) Bray, K. L.; Fairlamb, I. J. S.; Lloyd-Jones, G. C. Chem. Commun 2001, 187-188; (p) Kisanga, P.; Goj, L. A.; Widenhoefer, R. A. J. Org. Chem. 2001, 66, 635-637; (q) Oh, C. H.; Kim, J. D.; Han, J. W. Chem. Lett. 2001, 1290-1291; (r) Goj, L. A.; Widenhoefer, R. A. J. Am. Chem. Soc. 2001, 123, 11133-11147.
28. Recently Brummond's and Shibata's groups independently found that the analogous allenynes were cycloisomerized by rhodium(I) catalysts, see: (a) Brummond, K. M.; Chen, H.; Sill, P.; You, L. J. Am. Chem. Soc. 2002, 124, 15186-15187; (b) Shibata, T.; Takesue, Y.; Kadowaki, S.; Takagi, K. Synlett 2003, 268-270.
29. Recently Brummond's and Shibata's groups independently found that the analogous allenynes were cycloisomerized by rhodium(I) catalysts, see: (a) Brummond, K. M.; Chen, H.; Sill, P.; You, L. J. Am. Chem. Soc. 2002, 124, 15186-15187; (b) Shibata, T.; Takesue, Y.; Kadowaki, S.; Takagi, K. Synlett 2003, 268-270.
30. Previously, Wender et al. reported the related transition metal-catalyzed [4+2] cycloaddition of allenedienes and [5+2] cycloaddition of allene-vinylcyclopropanes, see: (a) Wender, P. A.; Jenkins, T. E.; Suzuki, S. J. Am. Chem. Soc. 1995, 117, 1843-1844; (b) Wender, P. A.; Glorius, F.; Husfeld, C. O.; Langkopf, E.; Love, J. A. J. Am. Chem. Soc. 1999, 121, 5348-5349.
31. Previously, Wender et al. reported the related transition metal-catalyzed [4+2] cycloaddition of allenedienes and [5+2] cycloaddition of allene-vinylcyclopropanes, see: (a) Wender, P. A.; Jenkins, T. E.; Suzuki, S. J. Am. Chem. Soc. 1995, 117, 1843-1844; (b) Wender, P. A.; Glorius, F.; Husfeld, C. O.; Langkopf, E.; Love, J. A. J. Am. Chem. Soc. 1999, 121, 5348-5349.
32. Trost B.M., Tour J.M. J. Am. Chem. Soc. 110:1988;5231-5233.
33. Trost B.M., Matsuda K. J. Am. Chem. Soc. 110:1988;5233-5235.
34. Kang S.-K., Ko B.-S., Lee D.-M. Tetrahedron Lett. 43:2002;6693-6696.
35. 4: 252.1362. Found: 252.1329.
36. The purity was determined by GC analysis of the isolated product 2. The recovered allenene 1 was included in the impurity.
37. 3 (9.4 mg, 0.027 mmol) in degassed dry 1,4-dioxane (1 ml). Then a solution of dimethyl 2-(4-methyl-2,3-pentadienyl)-2-(2-propenyl)malonate (1) (62.1 mg, 0.25 mmol) in degassed dry 1,4-dioxane (1.5 ml) was added to the reaction vessel. The mixture was stirred at 110°C for 18 h under an Ar atmosphere. After cooling to room temperature, the volatile materials were removed in vacuo. The residue was subjected to silica gel flash column chromatography (eluent; n-hexane/ethyl acetate=20/1) to afford dimethyl 3-methylene-4-(2-methyl-1-propenyl)cyclopentane-1,1-dicarboxylate (2) (56.9 mg, 92%) as colorless oil. The gas chromatographic analysis of the isolated product revealed that 2 was contained in 99% purity.
38. In the case of 7, the structure of side products are not determined at present.
39. The stereochemistry of 10 and 12 were determined by NOE experiments.
40. In the case of the cycloisomerization of allenynes, the allene moiety coordinates to the rhodium(I) center at the external allenic π-bond to form the rhodacyclopentene. See Ref. 6.
41. 3 slightly lowered both yield and purity of 20 (90% yield and 87% purity).
42. 4: C, 66.65; H, 7.99. Found: C, 66.51; H, 8.01.
43. Recently, Trost et al. reported the formation of exo-alkylidenecycloheptenes by the ruthenium-catalyzed cyclo-isomerization of 1,6-enynes, see: (a) Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 1999, 121, 9728; (b) Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 2002, 124, 5025. Similar mechanism is considered to also be operative in the present case.
44. Recently, Trost et al. reported the formation of exo-alkylidenecycloheptenes by the ruthenium-catalyzed cyclo-isomerization of 1,6-enynes, see: (a) Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 1999, 121, 9728; (b) Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 2002, 124, 5025. Similar mechanism is considered to also be operative in the present case.
45. Similar results were obtained in the transition metal-catalyzed carbonylative [4+1] cycloaddition of vinylallenes and [5+1] cycloaddition of allenylcyclopropanes, see: (a) Murakami, M.; Itami, K.; Ito, Y. Organometallics 1999, 18, 1326-1336; (b) Murakami, M.; Itami, K.; Ito, Y. J. Org. Chem. 1998, 63, 4-5.
46. Similar results were obtained in the transition metal-catalyzed carbonylative [4+1] cycloaddition of vinylallenes and [5+1] cycloaddition of allenylcyclopropanes, see: (a) Murakami, M.; Itami, K.; Ito, Y. Organometallics 1999, 18, 1326-1336; (b) Murakami, M.; Itami, K.; Ito, Y. J. Org. Chem. 1998, 63, 4-5.