Designing the chiral ligand space around an early transition metal: Myrtanyl zirconocene

Journal of Organic Chemistry

Volumn 64, Issue 12, 1999, Pages 4525-4527

  Taber, Douglass F ^a   Balijepalli, Bharati ^a   Liu, Kuan Kai ^a   Kong, Sue ^a   Rheingold, Arnold L ^a   Askham, Fredric R ^a,b  

^a UNIVERSITY OF DELAWARE   (United States)

^b Boulder Scientific Company   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

LIGAND; METAL DERIVATIVE; TITANIUM DERIVATIVE; ZIRCONIUM DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL INTERACTION; CHIRALITY; COMPLEX FORMATION; CONFORMATIONAL TRANSITION; MOLECULAR MODEL; OXIDATION; POLYMERIZATION; RACEMIC MIXTURE; X RAY CRYSTALLOGRAPHY;

EID: 0033546270     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981669f     Document Type: Article

References (52)

1. For recent catalytic applications of 1 and its Ti analogue, see: (a) Hong, Y.; Kuntz, B. A.; Collins, S. Organometallics 1993, 12, 964. (b) Jaquith, J. B.; Guan, J.; Wang, S.; Collins, S. Organometallics 1995, 14, 1079. (c) Jaquith, J. B.; Levy, C. J.; Bondar, G. V.; Wang, S.; Collins, S. Organometallics 1998, 17, 914. (d) Willoughby, C. A.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 8952. (e) Carter, M. B.; Schiott, B.; Gutierrez, A.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 11667. (f) Didiuk, M. T.; Johannes, C. W.; Morken, J. P.; Hoveyda, A. H. J. Am. Chem. Soc. 1995, 117, 7097. (g) Verdauguer, X.; Lange, U. E. W.; Reding, M. T.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 6784. (h) Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 11688. (i) Yamaura, Y.; Hyakutake, M.; Mori, M. J. Am. Chem. Soc. 1997, 119, 7615. (j) Gansauer, A. Synlett. 1997, 363.
2. For recent catalytic applications of 1 and its Ti analogue, see: (a) Hong, Y.; Kuntz, B. A.; Collins, S. Organometallics 1993, 12, 964. (b) Jaquith, J. B.; Guan, J.; Wang, S.; Collins, S. Organometallics 1995, 14, 1079. (c) Jaquith, J. B.; Levy, C. J.; Bondar, G. V.; Wang, S.; Collins, S. Organometallics 1998, 17, 914. (d) Willoughby, C. A.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 8952. (e) Carter, M. B.; Schiott, B.; Gutierrez, A.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 11667. (f) Didiuk, M. T.; Johannes, C. W.; Morken, J. P.; Hoveyda, A. H. J. Am. Chem. Soc. 1995, 117, 7097. (g) Verdauguer, X.; Lange, U. E. W.; Reding, M. T.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 6784. (h) Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 11688. (i) Yamaura, Y.; Hyakutake, M.; Mori, M. J. Am. Chem. Soc. 1997, 119, 7615. (j) Gansauer, A. Synlett. 1997, 363.
3. For recent catalytic applications of 1 and its Ti analogue, see: (a) Hong, Y.; Kuntz, B. A.; Collins, S. Organometallics 1993, 12, 964. (b) Jaquith, J. B.; Guan, J.; Wang, S.; Collins, S. Organometallics 1995, 14, 1079. (c) Jaquith, J. B.; Levy, C. J.; Bondar, G. V.; Wang, S.; Collins, S. Organometallics 1998, 17, 914. (d) Willoughby, C. A.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 8952. (e) Carter, M. B.; Schiott, B.; Gutierrez, A.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 11667. (f) Didiuk, M. T.; Johannes, C. W.; Morken, J. P.; Hoveyda, A. H. J. Am. Chem. Soc. 1995, 117, 7097. (g) Verdauguer, X.; Lange, U. E. W.; Reding, M. T.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 6784. (h) Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 11688. (i) Yamaura, Y.; Hyakutake, M.; Mori, M. J. Am. Chem. Soc. 1997, 119, 7615. (j) Gansauer, A. Synlett. 1997, 363.
4. For recent catalytic applications of 1 and its Ti analogue, see: (a) Hong, Y.; Kuntz, B. A.; Collins, S. Organometallics 1993, 12, 964. (b) Jaquith, J. B.; Guan, J.; Wang, S.; Collins, S. Organometallics 1995, 14, 1079. (c) Jaquith, J. B.; Levy, C. J.; Bondar, G. V.; Wang, S.; Collins, S. Organometallics 1998, 17, 914. (d) Willoughby, C. A.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 8952. (e) Carter, M. B.; Schiott, B.; Gutierrez, A.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 11667. (f) Didiuk, M. T.; Johannes, C. W.; Morken, J. P.; Hoveyda, A. H. J. Am. Chem. Soc. 1995, 117, 7097. (g) Verdauguer, X.; Lange, U. E. W.; Reding, M. T.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 6784. (h) Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 11688. (i) Yamaura, Y.; Hyakutake, M.; Mori, M. J. Am. Chem. Soc. 1997, 119, 7615. (j) Gansauer, A. Synlett. 1997, 363.
5. For recent catalytic applications of 1 and its Ti analogue, see: (a) Hong, Y.; Kuntz, B. A.; Collins, S. Organometallics 1993, 12, 964. (b) Jaquith, J. B.; Guan, J.; Wang, S.; Collins, S. Organometallics 1995, 14, 1079. (c) Jaquith, J. B.; Levy, C. J.; Bondar, G. V.; Wang, S.; Collins, S. Organometallics 1998, 17, 914. (d) Willoughby, C. A.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 8952. (e) Carter, M. B.; Schiott, B.; Gutierrez, A.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 11667. (f) Didiuk, M. T.; Johannes, C. W.; Morken, J. P.; Hoveyda, A. H. J. Am. Chem. Soc. 1995, 117, 7097. (g) Verdauguer, X.; Lange, U. E. W.; Reding, M. T.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 6784. (h) Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 11688. (i) Yamaura, Y.; Hyakutake, M.; Mori, M. J. Am. Chem. Soc. 1997, 119, 7615. (j) Gansauer, A. Synlett. 1997, 363.
6. For recent catalytic applications of 1 and its Ti analogue, see: (a) Hong, Y.; Kuntz, B. A.; Collins, S. Organometallics 1993, 12, 964. (b) Jaquith, J. B.; Guan, J.; Wang, S.; Collins, S. Organometallics 1995, 14, 1079. (c) Jaquith, J. B.; Levy, C. J.; Bondar, G. V.; Wang, S.; Collins, S. Organometallics 1998, 17, 914. (d) Willoughby, C. A.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 8952. (e) Carter, M. B.; Schiott, B.; Gutierrez, A.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 11667. (f) Didiuk, M. T.; Johannes, C. W.; Morken, J. P.; Hoveyda, A. H. J. Am. Chem. Soc. 1995, 117, 7097. (g) Verdauguer, X.; Lange, U. E. W.; Reding, M. T.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 6784. (h) Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 11688. (i) Yamaura, Y.; Hyakutake, M.; Mori, M. J. Am. Chem. Soc. 1997, 119, 7615. (j) Gansauer, A. Synlett. 1997, 363.
7. For recent catalytic applications of 1 and its Ti analogue, see: (a) Hong, Y.; Kuntz, B. A.; Collins, S. Organometallics 1993, 12, 964. (b) Jaquith, J. B.; Guan, J.; Wang, S.; Collins, S. Organometallics 1995, 14, 1079. (c) Jaquith, J. B.; Levy, C. J.; Bondar, G. V.; Wang, S.; Collins, S. Organometallics 1998, 17, 914. (d) Willoughby, C. A.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 8952. (e) Carter, M. B.; Schiott, B.; Gutierrez, A.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 11667. (f) Didiuk, M. T.; Johannes, C. W.; Morken, J. P.; Hoveyda, A. H. J. Am. Chem. Soc. 1995, 117, 7097. (g) Verdauguer, X.; Lange, U. E. W.; Reding, M. T.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 6784. (h) Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 11688. (i) Yamaura, Y.; Hyakutake, M.; Mori, M. J. Am. Chem. Soc. 1997, 119, 7615. (j) Gansauer, A. Synlett. 1997, 363.
8. For recent catalytic applications of 1 and its Ti analogue, see: (a) Hong, Y.; Kuntz, B. A.; Collins, S. Organometallics 1993, 12, 964. (b) Jaquith, J. B.; Guan, J.; Wang, S.; Collins, S. Organometallics 1995, 14, 1079. (c) Jaquith, J. B.; Levy, C. J.; Bondar, G. V.; Wang, S.; Collins, S. Organometallics 1998, 17, 914. (d) Willoughby, C. A.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 8952. (e) Carter, M. B.; Schiott, B.; Gutierrez, A.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 11667. (f) Didiuk, M. T.; Johannes, C. W.; Morken, J. P.; Hoveyda, A. H. J. Am. Chem. Soc. 1995, 117, 7097. (g) Verdauguer, X.; Lange, U. E. W.; Reding, M. T.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 6784. (h) Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 11688. (i) Yamaura, Y.; Hyakutake, M.; Mori, M. J. Am. Chem. Soc. 1997, 119, 7615. (j) Gansauer, A. Synlett. 1997, 363.
9. For recent catalytic applications of 1 and its Ti analogue, see: (a) Hong, Y.; Kuntz, B. A.; Collins, S. Organometallics 1993, 12, 964. (b) Jaquith, J. B.; Guan, J.; Wang, S.; Collins, S. Organometallics 1995, 14, 1079. (c) Jaquith, J. B.; Levy, C. J.; Bondar, G. V.; Wang, S.; Collins, S. Organometallics 1998, 17, 914. (d) Willoughby, C. A.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 8952. (e) Carter, M. B.; Schiott, B.; Gutierrez, A.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 11667. (f) Didiuk, M. T.; Johannes, C. W.; Morken, J. P.; Hoveyda, A. H. J. Am. Chem. Soc. 1995, 117, 7097. (g) Verdauguer, X.; Lange, U. E. W.; Reding, M. T.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 6784. (h) Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 11688. (i) Yamaura, Y.; Hyakutake, M.; Mori, M. J. Am. Chem. Soc. 1997, 119, 7615. (j) Gansauer, A. Synlett. 1997, 363.
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17. For leading references to the use of 1 in the polymerization of α-olefins, see: (a) Castonguay, L. A.; Rappe, A. K. J. Am. Chem. Soc. 1992, 114, 5832. (b) Coates, G. W.; Waymouth, R. M. J. Am. Chem. Soc. 1998, 115, 91. (c) Erker, G.; Aulbach, M.; Knickmeier, M.; Wingbermuhle, D.; Kruger, K.; Nolte, M.; Werner, S. J. Am. Chem. Soc. 1993, 115, 4590. (d) Guerra, G.; Cavallo, L.; Moscardi, G.; Vacatello, M.; Corradini, P. J. Am. Chem. Soc. 1994, 116, 2988. (e) Rodewald, S.; Jordan, R. F. J. Am. Chem. Soc. 1994, 116, 4491. (f) Leclerc, M. K.; Brintzinger, H. H. J. Am. Chem. Soc. 1995, 117, 1651.
18. For leading references to the use of 1 in the polymerization of α-olefins, see: (a) Castonguay, L. A.; Rappe, A. K. J. Am. Chem. Soc. 1992, 114, 5832. (b) Coates, G. W.; Waymouth, R. M. J. Am. Chem. Soc. 1998, 115, 91. (c) Erker, G.; Aulbach, M.; Knickmeier, M.; Wingbermuhle, D.; Kruger, K.; Nolte, M.; Werner, S. J. Am. Chem. Soc. 1993, 115, 4590. (d) Guerra, G.; Cavallo, L.; Moscardi, G.; Vacatello, M.; Corradini, P. J. Am. Chem. Soc. 1994, 116, 2988. (e) Rodewald, S.; Jordan, R. F. J. Am. Chem. Soc. 1994, 116, 4491. (f) Leclerc, M. K.; Brintzinger, H. H. J. Am. Chem. Soc. 1995, 117, 1651.
19. For leading references to the use of 1 in the polymerization of α-olefins, see: (a) Castonguay, L. A.; Rappe, A. K. J. Am. Chem. Soc. 1992, 114, 5832. (b) Coates, G. W.; Waymouth, R. M. J. Am. Chem. Soc. 1998, 115, 91. (c) Erker, G.; Aulbach, M.; Knickmeier, M.; Wingbermuhle, D.; Kruger, K.; Nolte, M.; Werner, S. J. Am. Chem. Soc. 1993, 115, 4590. (d) Guerra, G.; Cavallo, L.; Moscardi, G.; Vacatello, M.; Corradini, P. J. Am. Chem. Soc. 1994, 116, 2988. (e) Rodewald, S.; Jordan, R. F. J. Am. Chem. Soc. 1994, 116, 4491. (f) Leclerc, M. K.; Brintzinger, H. H. J. Am. Chem. Soc. 1995, 117, 1651.
20. For leading references to the use of 1 in the polymerization of α-olefins, see: (a) Castonguay, L. A.; Rappe, A. K. J. Am. Chem. Soc. 1992, 114, 5832. (b) Coates, G. W.; Waymouth, R. M. J. Am. Chem. Soc. 1998, 115, 91. (c) Erker, G.; Aulbach, M.; Knickmeier, M.; Wingbermuhle, D.; Kruger, K.; Nolte, M.; Werner, S. J. Am. Chem. Soc. 1993, 115, 4590. (d) Guerra, G.; Cavallo, L.; Moscardi, G.; Vacatello, M.; Corradini, P. J. Am. Chem. Soc. 1994, 116, 2988. (e) Rodewald, S.; Jordan, R. F. J. Am. Chem. Soc. 1994, 116, 4491. (f) Leclerc, M. K.; Brintzinger, H. H. J. Am. Chem. Soc. 1995, 117, 1651.
21. For leading references to the use of 1 in the polymerization of α-olefins, see: (a) Castonguay, L. A.; Rappe, A. K. J. Am. Chem. Soc. 1992, 114, 5832. (b) Coates, G. W.; Waymouth, R. M. J. Am. Chem. Soc. 1998, 115, 91. (c) Erker, G.; Aulbach, M.; Knickmeier, M.; Wingbermuhle, D.; Kruger, K.; Nolte, M.; Werner, S. J. Am. Chem. Soc. 1993, 115, 4590. (d) Guerra, G.; Cavallo, L.; Moscardi, G.; Vacatello, M.; Corradini, P. J. Am. Chem. Soc. 1994, 116, 2988. (e) Rodewald, S.; Jordan, R. F. J. Am. Chem. Soc. 1994, 116, 4491. (f) Leclerc, M. K.; Brintzinger, H. H. J. Am. Chem. Soc. 1995, 117, 1651.
22. (a) For a review of alternative inherently chiral bis-Cp systems, see: Halterman, R. L. Chem. Rev. 1992, 92, 965. For more recent references, see (b) Chen, Z.; Halterman, R. L. J. Am. Chem. Soc. 1992, 114, 2276. (c) Halterman, R. L.; Ramsey, T. M.; Chen, Z. J. Org. Chem. 1994, 59, 2642. (d) Giardello, M. A.; Yamamoto, Y.; Brard, L.; Marks, T. J. J. Am. Chem. Soc. 1995, 117, 3276. (e) Urabe, H.; Yoshikawa, K.; Sato, F. Tetrahedron Lett. 1995, 36, 5595. (f) Mitchell, J. P.; Hajela, S.; Brookhart, S. K.; Hardcastle, K. L.; Herding, L. M.; Bercaw, J. E. J. Am. Chem. Soc. 1996, 118, 1045. (g) Bell, L.; Whitby, R. J.; Jones, R. V. H.; Standen, M. C. H. Tetrahedron Lett. 1996, 37, 7139. (h) Liu, C.; Sowa, J. R., Jr. Tetrahedron Lett. 1996, 37, 7241.
23. (a) For a review of alternative inherently chiral bis-Cp systems, see: Halterman, R. L. Chem. Rev. 1992, 92, 965. For more recent references, see (b) Chen, Z.; Halterman, R. L. J. Am. Chem. Soc. 1992, 114, 2276. (c) Halterman, R. L.; Ramsey, T. M.; Chen, Z. J. Org. Chem. 1994, 59, 2642. (d) Giardello, M. A.; Yamamoto, Y.; Brard, L.; Marks, T. J. J. Am. Chem. Soc. 1995, 117, 3276. (e) Urabe, H.; Yoshikawa, K.; Sato, F. Tetrahedron Lett. 1995, 36, 5595. (f) Mitchell, J. P.; Hajela, S.; Brookhart, S. K.; Hardcastle, K. L.; Herding, L. M.; Bercaw, J. E. J. Am. Chem. Soc. 1996, 118, 1045. (g) Bell, L.; Whitby, R. J.; Jones, R. V. H.; Standen, M. C. H. Tetrahedron Lett. 1996, 37, 7139. (h) Liu, C.; Sowa, J. R., Jr. Tetrahedron Lett. 1996, 37, 7241.
24. (a) For a review of alternative inherently chiral bis-Cp systems, see: Halterman, R. L. Chem. Rev. 1992, 92, 965. For more recent references, see (b) Chen, Z.; Halterman, R. L. J. Am. Chem. Soc. 1992, 114, 2276. (c) Halterman, R. L.; Ramsey, T. M.; Chen, Z. J. Org. Chem. 1994, 59, 2642. (d) Giardello, M. A.; Yamamoto, Y.; Brard, L.; Marks, T. J. J. Am. Chem. Soc. 1995, 117, 3276. (e) Urabe, H.; Yoshikawa, K.; Sato, F. Tetrahedron Lett. 1995, 36, 5595. (f) Mitchell, J. P.; Hajela, S.; Brookhart, S. K.; Hardcastle, K. L.; Herding, L. M.; Bercaw, J. E. J. Am. Chem. Soc. 1996, 118, 1045. (g) Bell, L.; Whitby, R. J.; Jones, R. V. H.; Standen, M. C. H. Tetrahedron Lett. 1996, 37, 7139. (h) Liu, C.; Sowa, J. R., Jr. Tetrahedron Lett. 1996, 37, 7241.
25. (a) For a review of alternative inherently chiral bis-Cp systems, see: Halterman, R. L. Chem. Rev. 1992, 92, 965. For more recent references, see (b) Chen, Z.; Halterman, R. L. J. Am. Chem. Soc. 1992, 114, 2276. (c) Halterman, R. L.; Ramsey, T. M.; Chen, Z. J. Org. Chem. 1994, 59, 2642. (d) Giardello, M. A.; Yamamoto, Y.; Brard, L.; Marks, T. J. J. Am. Chem. Soc. 1995, 117, 3276. (e) Urabe, H.; Yoshikawa, K.; Sato, F. Tetrahedron Lett. 1995, 36, 5595. (f) Mitchell, J. P.; Hajela, S.; Brookhart, S. K.; Hardcastle, K. L.; Herding, L. M.; Bercaw, J. E. J. Am. Chem. Soc. 1996, 118, 1045. (g) Bell, L.; Whitby, R. J.; Jones, R. V. H.; Standen, M. C. H. Tetrahedron Lett. 1996, 37, 7139. (h) Liu, C.; Sowa, J. R., Jr. Tetrahedron Lett. 1996, 37, 7241.
26. (a) For a review of alternative inherently chiral bis-Cp systems, see: Halterman, R. L. Chem. Rev. 1992, 92, 965. For more recent references, see (b) Chen, Z.; Halterman, R. L. J. Am. Chem. Soc. 1992, 114, 2276. (c) Halterman, R. L.; Ramsey, T. M.; Chen, Z. J. Org. Chem. 1994, 59, 2642. (d) Giardello, M. A.; Yamamoto, Y.; Brard, L.; Marks, T. J. J. Am. Chem. Soc. 1995, 117, 3276. (e) Urabe, H.; Yoshikawa, K.; Sato, F. Tetrahedron Lett. 1995, 36, 5595. (f) Mitchell, J. P.; Hajela, S.; Brookhart, S. K.; Hardcastle, K. L.; Herding, L. M.; Bercaw, J. E. J. Am. Chem. Soc. 1996, 118, 1045. (g) Bell, L.; Whitby, R. J.; Jones, R. V. H.; Standen, M. C. H. Tetrahedron Lett. 1996, 37, 7139. (h) Liu, C.; Sowa, J. R., Jr. Tetrahedron Lett. 1996, 37, 7241.
27. (a) For a review of alternative inherently chiral bis-Cp systems, see: Halterman, R. L. Chem. Rev. 1992, 92, 965. For more recent references, see (b) Chen, Z.; Halterman, R. L. J. Am. Chem. Soc. 1992, 114, 2276. (c) Halterman, R. L.; Ramsey, T. M.; Chen, Z. J. Org. Chem. 1994, 59, 2642. (d) Giardello, M. A.; Yamamoto, Y.; Brard, L.; Marks, T. J. J. Am. Chem. Soc. 1995, 117, 3276. (e) Urabe, H.; Yoshikawa, K.; Sato, F. Tetrahedron Lett. 1995, 36, 5595. (f) Mitchell, J. P.; Hajela, S.; Brookhart, S. K.; Hardcastle, K. L.; Herding, L. M.; Bercaw, J. E. J. Am. Chem. Soc. 1996, 118, 1045. (g) Bell, L.; Whitby, R. J.; Jones, R. V. H.; Standen, M. C. H. Tetrahedron Lett. 1996, 37, 7139. (h) Liu, C.; Sowa, J. R., Jr. Tetrahedron Lett. 1996, 37, 7241.
28. (a) For a review of alternative inherently chiral bis-Cp systems, see: Halterman, R. L. Chem. Rev. 1992, 92, 965. For more recent references, see (b) Chen, Z.; Halterman, R. L. J. Am. Chem. Soc. 1992, 114, 2276. (c) Halterman, R. L.; Ramsey, T. M.; Chen, Z. J. Org. Chem. 1994, 59, 2642. (d) Giardello, M. A.; Yamamoto, Y.; Brard, L.; Marks, T. J. J. Am. Chem. Soc. 1995, 117, 3276. (e) Urabe, H.; Yoshikawa, K.; Sato, F. Tetrahedron Lett. 1995, 36, 5595. (f) Mitchell, J. P.; Hajela, S.; Brookhart, S. K.; Hardcastle, K. L.; Herding, L. M.; Bercaw, J. E. J. Am. Chem. Soc. 1996, 118, 1045. (g) Bell, L.; Whitby, R. J.; Jones, R. V. H.; Standen, M. C. H. Tetrahedron Lett. 1996, 37, 7139. (h) Liu, C.; Sowa, J. R., Jr. Tetrahedron Lett. 1996, 37, 7241.
29. (a) For a review of alternative inherently chiral bis-Cp systems, see: Halterman, R. L. Chem. Rev. 1992, 92, 965. For more recent references, see (b) Chen, Z.; Halterman, R. L. J. Am. Chem. Soc. 1992, 114, 2276. (c) Halterman, R. L.; Ramsey, T. M.; Chen, Z. J. Org. Chem. 1994, 59, 2642. (d) Giardello, M. A.; Yamamoto, Y.; Brard, L.; Marks, T. J. J. Am. Chem. Soc. 1995, 117, 3276. (e) Urabe, H.; Yoshikawa, K.; Sato, F. Tetrahedron Lett. 1995, 36, 5595. (f) Mitchell, J. P.; Hajela, S.; Brookhart, S. K.; Hardcastle, K. L.; Herding, L. M.; Bercaw, J. E. J. Am. Chem. Soc. 1996, 118, 1045. (g) Bell, L.; Whitby, R. J.; Jones, R. V. H.; Standen, M. C. H. Tetrahedron Lett. 1996, 37, 7139. (h) Liu, C.; Sowa, J. R., Jr. Tetrahedron Lett. 1996, 37, 7241.
30. (a) Paquette, L. A.; Moriarty, K. J.; Rogers, R. D. Organometallics 1989, 8, 1506.
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32. Both ZINDO and molecular mechanics were used as implemented on the Tektronix CAChe workstation. For leading references to ZINDO, a semiempirical program that has been parametrized for the first two rows of transition metals, see: (a) Zerner, M. C.; Loew, G. W.; Kirchner, R. F.; Mueller-Westerhoff, U. T. J. Am. Chem. Soc. 1980, 102, 589. (b) Anderson, W. P.; Cundari, T. R.; Drago, R. S.; Zerner, M. C. Inorg. Chem. 1990, 29, 1.
33. Both ZINDO and molecular mechanics were used as implemented on the Tektronix CAChe workstation. For leading references to ZINDO, a semiempirical program that has been parametrized for the first two rows of transition metals, see: (a) Zerner, M. C.; Loew, G. W.; Kirchner, R. F.; Mueller-Westerhoff, U. T. J. Am. Chem. Soc. 1980, 102, 589. (b) Anderson, W. P.; Cundari, T. R.; Drago, R. S.; Zerner, M. C. Inorg. Chem. 1990, 29, 1.
34. For related experimental/computational studies of intramolecular diene cyclozirconation, see: (a) Taber, D. F.; Louey, J. P.; Wang, Y.; Nugent, W. A.; Dixon, D. A.; Harlow, R. L. J. Am. Chem. Soc. 1994, 116, 9457. (b) Taber, D. F.; Louey, J. P. Tetrahedron 1995, 51, 4495. (c) Taber, D. F.; Wang, Y. Tetrahedron Lett. 1995, 36, 6639.
35. For related experimental/computational studies of intramolecular diene cyclozirconation, see: (a) Taber, D. F.; Louey, J. P.; Wang, Y.; Nugent, W. A.; Dixon, D. A.; Harlow, R. L. J. Am. Chem. Soc. 1994, 116, 9457. (b) Taber, D. F.; Louey, J. P. Tetrahedron 1995, 51, 4495. (c) Taber, D. F.; Wang, Y. Tetrahedron Lett. 1995, 36, 6639.
36. For related experimental/computational studies of intramolecular diene cyclozirconation, see: (a) Taber, D. F.; Louey, J. P.; Wang, Y.; Nugent, W. A.; Dixon, D. A.; Harlow, R. L. J. Am. Chem. Soc. 1994, 116, 9457. (b) Taber, D. F.; Louey, J. P. Tetrahedron 1995, 51, 4495. (c) Taber, D. F.; Wang, Y. Tetrahedron Lett. 1995, 36, 6639.
37. For analogous experimental/computational studies of Rh-mediated intramolecular C-H insertion and Rh(II) tetracarboxylate design, see: (a) Taber, D. F.; You, K. K. J. Am. Chem. Soc. 1995, 117, 5757. (b) Taber, D. F.: You. K. K.; Rheingold, A. L. J. Am. Chem. Soc. 1996, 118, 547. (c) Taber, D. F.; Meagley, R. P.; Louey, J. P.; Rheingold, A. L. Inorg. Chim. Acta 1996, 239, 25.
38. For analogous experimental/computational studies of Rh-mediated intramolecular C-H insertion and Rh(II) tetracarboxylate design, see: (a) Taber, D. F.; You, K. K. J. Am. Chem. Soc. 1995, 117, 5757. (b) Taber, D. F.: You. K. K.; Rheingold, A. L. J. Am. Chem. Soc. 1996, 118, 547. (c) Taber, D. F.; Meagley, R. P.; Louey, J. P.; Rheingold, A. L. Inorg. Chim. Acta 1996, 239, 25.
39. For analogous experimental/computational studies of Rh-mediated intramolecular C-H insertion and Rh(II) tetracarboxylate design, see: (a) Taber, D. F.; You, K. K. J. Am. Chem. Soc. 1995, 117, 5757. (b) Taber, D. F.: You. K. K.; Rheingold, A. L. J. Am. Chem. Soc. 1996, 118, 547. (c) Taber, D. F.; Meagley, R. P.; Louey, J. P.; Rheingold, A. L. Inorg. Chim. Acta 1996, 239, 25.
40. Although only (R)-myrtenal is commercially available, (S)-myrtenal can be prepared in one step by oxidation of α-pinene: Barton, D. H. R.; Wang, T.-L. Tetrahedron Lett. 1994, 35, 5149.
41. Sutton, S. C.; Nantz, M. H.; Parkin, S. R. Organometallics 1993, 12, 2248.
42. (a) Skattebol, L. Tetrahedron, 1967, 23, 1107; J. Org. Chem. 1964, 29, 2951.
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46. For a detailed discussion of the Skattebol rearrangement, see: Boche, G.; Walborsky, H. M. Cyclopropane Derived Reactive Intermediates; John Wiley and Sons: New York, 1990; pp 175-205, and references therein.
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48. Ito, Y.; Komolke, T.; Saegusa, T. J. Am. Chem. Soc. 1975, 97, 2912.
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50. (b) Seyferth, D.; Lambert, R. L., Jr. J. Organomet. Chem. 1969, 16, 21.
51. 3, Z = 4, T = 232 K. R(F) = 3.64%, R(wF) = 3.55%.
52. For general experimental procedures, see: Taber, D. F.; Meagley, R. P.; Doren, D. J. J. Org. Chem. 1996, 61, 5723.