Ruthenium-catalyzed silyl ether formation and enyne metathesis sequence: Synthesis of siloxacycles from terminal alkenyl alcohols and alkynylsilanes

Organic Letters

Volumn 6, Issue 16, 2004, Pages 2773-2776

  Miller, Reagan L ^a   Maifeld, Sarah V ^a   Lee, Daesung ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ALKENYL GROUP; HYDROGEN; RUTHENIUM; SILANE DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; DEHYDROGENATION; POLYMERIZATION; RING CLOSING METATHESIS; SYNTHESIS;

ALCOHOLS; ALKENES; ALKYNES; CATALYSIS; ETHERS; MOLECULAR STRUCTURE; RUTHENIUM; SILANES; SILOXANES;

EID: 4143116942     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol049019n     Document Type: Article

References (69)

1. For recent reviews of enyne metathesis, see: (a) Mori, M. Top. Organomet. Chem. 1998, 1, 133. (b) Poulsen, C. S.; Madsen, R. Synthesis 2003, 1. (c) Mori, M. In Handbook of Metathesis; Grubbs, R. H., Ed.; Wiley-VCH: Weinheim, Germany, 2003; Vol. 2, pp 176-204. (d) Giessert, A. J.; Diver, S. T. Chem. Rev. 2004, 104, 1317.
2. For recent reviews of enyne metathesis, see: (a) Mori, M. Top. Organomet. Chem. 1998, 1, 133. (b) Poulsen, C. S.; Madsen, R. Synthesis 2003, 1. (c) Mori, M. In Handbook of Metathesis; Grubbs, R. H., Ed.; Wiley-VCH: Weinheim, Germany, 2003; Vol. 2, pp 176-204. (d) Giessert, A. J.; Diver, S. T. Chem. Rev. 2004, 104, 1317.
3. For recent reviews of enyne metathesis, see: (a) Mori, M. Top. Organomet. Chem. 1998, 1, 133. (b) Poulsen, C. S.; Madsen, R. Synthesis 2003, 1. (c) Mori, M. In Handbook of Metathesis; Grubbs, R. H., Ed.; Wiley-VCH: Weinheim, Germany, 2003; Vol. 2, pp 176-204. (d) Giessert, A. J.; Diver, S. T. Chem. Rev. 2004, 104, 1317.
4. For recent reviews of enyne metathesis, see: (a) Mori, M. Top. Organomet. Chem. 1998, 1, 133. (b) Poulsen, C. S.; Madsen, R. Synthesis 2003, 1. (c) Mori, M. In Handbook of Metathesis; Grubbs, R. H., Ed.; Wiley-VCH: Weinheim, Germany, 2003; Vol. 2, pp 176-204. (d) Giessert, A. J.; Diver, S. T. Chem. Rev. 2004, 104, 1317.
5. (a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413.
6. (b) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371.
7. (c) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3013.
8. (d) Connon, S. J.; Blechert, S. Angew. Chem., Int. Ed. 2003, 42, 1900.
9. (e) Schrock, R. R.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2003, 42, 4592.
10. (a) Katz, T. J.; McGinnis, J. J. Am. Chem. Soc. 1975, 97, 1592.
11. (b) Wengrovius, J. H.; Sancho, J. J. Am. Chem. Soc. 1981, 103, 3932.
12. (c) Schrock, R. R.; Clark, D. N.; Sancho, J.; Wengrovius, J. H.; Rocklage, S. M.; Pedersen, S. F. Organometallics 1982, 1, 1645.
13. (d) Fürstner, A.; Seidel, G. Angew. Chem., Int. Ed. 1998, 37, 1734.
14. (e) Fürstner, A.; Guth, O.; Rumbo, A.; Seidel, G. J. Am. Chem. Soc. 1999, 121, 11108.
15. Examples of completed total synthesis of natural products with enyne metathesis as a key step, see: (a) Kinoshita, A.; Mori, M. J. Org. Chem. 1996, 61, 8356. (b) Hoye, T. R.; Donaldson, S. M.; Vos, T. J. Org. Lett. 1999, 1, 277. (c) Mori, M.; Tonogaki, K.; Nishiguchi, N. J. Org. Chem. 2002, 67, 224. (d) Layton, M. E.; Morales, C. A.; Shair, M. D. J. Am. Chem. Soc. 2002, 124, 773. (e) Fukumoto, H.; Esumi, T.; Ishihara, J.; Hatakeyama, S. Tetrahedron Lett. 2003, 44, 8047. (f) Brennema, J. B.; Martin, S. F. Org. Lett. 2004, 6, 1329. (g) Aggarwal, V. K.; Astle, C. J.; Rogers-Evans, M. Org. Lett. 2004, 6, 1469. (h) Mori, M.; Tomita, T.; Kita, Y.; Kitamura, T. Tetrahedron Lett. 2004, 45, 4397.
16. Examples of completed total synthesis of natural products with enyne metathesis as a key step, see: (a) Kinoshita, A.; Mori, M. J. Org. Chem. 1996, 61, 8356. (b) Hoye, T. R.; Donaldson, S. M.; Vos, T. J. Org. Lett. 1999, 1, 277. (c) Mori, M.; Tonogaki, K.; Nishiguchi, N. J. Org. Chem. 2002, 67, 224. (d) Layton, M. E.; Morales, C. A.; Shair, M. D. J. Am. Chem. Soc. 2002, 124, 773. (e) Fukumoto, H.; Esumi, T.; Ishihara, J.; Hatakeyama, S. Tetrahedron Lett. 2003, 44, 8047. (f) Brennema, J. B.; Martin, S. F. Org. Lett. 2004, 6, 1329. (g) Aggarwal, V. K.; Astle, C. J.; Rogers-Evans, M. Org. Lett. 2004, 6, 1469. (h) Mori, M.; Tomita, T.; Kita, Y.; Kitamura, T. Tetrahedron Lett. 2004, 45, 4397.
17. Examples of completed total synthesis of natural products with enyne metathesis as a key step, see: (a) Kinoshita, A.; Mori, M. J. Org. Chem. 1996, 61, 8356. (b) Hoye, T. R.; Donaldson, S. M.; Vos, T. J. Org. Lett. 1999, 1, 277. (c) Mori, M.; Tonogaki, K.; Nishiguchi, N. J. Org. Chem. 2002, 67, 224. (d) Layton, M. E.; Morales, C. A.; Shair, M. D. J. Am. Chem. Soc. 2002, 124, 773. (e) Fukumoto, H.; Esumi, T.; Ishihara, J.; Hatakeyama, S. Tetrahedron Lett. 2003, 44, 8047. (f) Brennema, J. B.; Martin, S. F. Org. Lett. 2004, 6, 1329. (g) Aggarwal, V. K.; Astle, C. J.; Rogers-Evans, M. Org. Lett. 2004, 6, 1469. (h) Mori, M.; Tomita, T.; Kita, Y.; Kitamura, T. Tetrahedron Lett. 2004, 45, 4397.
18. Examples of completed total synthesis of natural products with enyne metathesis as a key step, see: (a) Kinoshita, A.; Mori, M. J. Org. Chem. 1996, 61, 8356. (b) Hoye, T. R.; Donaldson, S. M.; Vos, T. J. Org. Lett. 1999, 1, 277. (c) Mori, M.; Tonogaki, K.; Nishiguchi, N. J. Org. Chem. 2002, 67, 224. (d) Layton, M. E.; Morales, C. A.; Shair, M. D. J. Am. Chem. Soc. 2002, 124, 773. (e) Fukumoto, H.; Esumi, T.; Ishihara, J.; Hatakeyama, S. Tetrahedron Lett. 2003, 44, 8047. (f) Brennema, J. B.; Martin, S. F. Org. Lett. 2004, 6, 1329. (g) Aggarwal, V. K.; Astle, C. J.; Rogers-Evans, M. Org. Lett. 2004, 6, 1469. (h) Mori, M.; Tomita, T.; Kita, Y.; Kitamura, T. Tetrahedron Lett. 2004, 45, 4397.
19. Examples of completed total synthesis of natural products with enyne metathesis as a key step, see: (a) Kinoshita, A.; Mori, M. J. Org. Chem. 1996, 61, 8356. (b) Hoye, T. R.; Donaldson, S. M.; Vos, T. J. Org. Lett. 1999, 1, 277. (c) Mori, M.; Tonogaki, K.; Nishiguchi, N. J. Org. Chem. 2002, 67, 224. (d) Layton, M. E.; Morales, C. A.; Shair, M. D. J. Am. Chem. Soc. 2002, 124, 773. (e) Fukumoto, H.; Esumi, T.; Ishihara, J.; Hatakeyama, S. Tetrahedron Lett. 2003, 44, 8047. (f) Brennema, J. B.; Martin, S. F. Org. Lett. 2004, 6, 1329. (g) Aggarwal, V. K.; Astle, C. J.; Rogers-Evans, M. Org. Lett. 2004, 6, 1469. (h) Mori, M.; Tomita, T.; Kita, Y.; Kitamura, T. Tetrahedron Lett. 2004, 45, 4397.
20. Examples of completed total synthesis of natural products with enyne metathesis as a key step, see: (a) Kinoshita, A.; Mori, M. J. Org. Chem. 1996, 61, 8356. (b) Hoye, T. R.; Donaldson, S. M.; Vos, T. J. Org. Lett. 1999, 1, 277. (c) Mori, M.; Tonogaki, K.; Nishiguchi, N. J. Org. Chem. 2002, 67, 224. (d) Layton, M. E.; Morales, C. A.; Shair, M. D. J. Am. Chem. Soc. 2002, 124, 773. (e) Fukumoto, H.; Esumi, T.; Ishihara, J.; Hatakeyama, S. Tetrahedron Lett. 2003, 44, 8047. (f) Brennema, J. B.; Martin, S. F. Org. Lett. 2004, 6, 1329. (g) Aggarwal, V. K.; Astle, C. J.; Rogers-Evans, M. Org. Lett. 2004, 6, 1469. (h) Mori, M.; Tomita, T.; Kita, Y.; Kitamura, T. Tetrahedron Lett. 2004, 45, 4397.
21. Examples of completed total synthesis of natural products with enyne metathesis as a key step, see: (a) Kinoshita, A.; Mori, M. J. Org. Chem. 1996, 61, 8356. (b) Hoye, T. R.; Donaldson, S. M.; Vos, T. J. Org. Lett. 1999, 1, 277. (c) Mori, M.; Tonogaki, K.; Nishiguchi, N. J. Org. Chem. 2002, 67, 224. (d) Layton, M. E.; Morales, C. A.; Shair, M. D. J. Am. Chem. Soc. 2002, 124, 773. (e) Fukumoto, H.; Esumi, T.; Ishihara, J.; Hatakeyama, S. Tetrahedron Lett. 2003, 44, 8047. (f) Brennema, J. B.; Martin, S. F. Org. Lett. 2004, 6, 1329. (g) Aggarwal, V. K.; Astle, C. J.; Rogers-Evans, M. Org. Lett. 2004, 6, 1469. (h) Mori, M.; Tomita, T.; Kita, Y.; Kitamura, T. Tetrahedron Lett. 2004, 45, 4397.
22. Examples of completed total synthesis of natural products with enyne metathesis as a key step, see: (a) Kinoshita, A.; Mori, M. J. Org. Chem. 1996, 61, 8356. (b) Hoye, T. R.; Donaldson, S. M.; Vos, T. J. Org. Lett. 1999, 1, 277. (c) Mori, M.; Tonogaki, K.; Nishiguchi, N. J. Org. Chem. 2002, 67, 224. (d) Layton, M. E.; Morales, C. A.; Shair, M. D. J. Am. Chem. Soc. 2002, 124, 773. (e) Fukumoto, H.; Esumi, T.; Ishihara, J.; Hatakeyama, S. Tetrahedron Lett. 2003, 44, 8047. (f) Brennema, J. B.; Martin, S. F. Org. Lett. 2004, 6, 1329. (g) Aggarwal, V. K.; Astle, C. J.; Rogers-Evans, M. Org. Lett. 2004, 6, 1469. (h) Mori, M.; Tomita, T.; Kita, Y.; Kitamura, T. Tetrahedron Lett. 2004, 45, 4397.
23. Other heteroatom-containing enyne RCM, see the following. With boron: (a) Micalizio, G.; Schreiber, S. L. Angew. Chem., Int. Ed. 2002, 41, 3272. (b) Renaud, J.; Graf, C.-D.; Oberer, L. Angew. Chem., Int. Ed. 2000, 39, 3101. With nitrogen: (c) Huang, J.; Xiong, H.; Hsung, R. P.; Rameshkumar, C.; Mulder, J. A.; Grebe, T. P. Org. Lett. 2002, 4, 2417. (d) Saito, N.; Sato, Y.; Mori, M. Org. Lett. 2002, 4, 803. With oxygen: (e) Clark, J. S.; Trevitt, G. P.; Boyall, D.; Stammen, B. Chem. Commun. 1998, 2629. (f) Clark, J. S.; Elustondo, F.; Trevitt, G. P.; Boyall, D.; Robertson, J.; Blake, A. J.; Wilson, C.; Stammen, B. Tetrahedron 2002, 58, 1973. (g) Schramm, M. P.; Reddy, D. S.; Kozmin, S. A. Angew. Chem., Int. Ed. 2001, 40, 4274. (h) Reddy, D. S.; Kozmin, S. A. J. Org. Chem. published online June 12, http://dx.doi.org/10.1021/jo049431g. With phosphorous: Schramm, M. P.; Reddy, D. S.; Kozmin, S. Angew. Chem., Int. Ed. 2002, 40, 4274. With phosphorus: (i) Timmer, M. S. M.; Ovaa, H.; Filippov, D. V.; van der Marel, G. A.; van Boom, J. H. Tetrahedron Lett. 2001, 42, 8231.
24. Other heteroatom-containing enyne RCM, see the following. With boron: (a) Micalizio, G.; Schreiber, S. L. Angew. Chem., Int. Ed. 2002, 41, 3272. (b) Renaud, J.; Graf, C.-D.; Oberer, L. Angew. Chem., Int. Ed. 2000, 39, 3101. With nitrogen: (c) Huang, J.; Xiong, H.; Hsung, R. P.; Rameshkumar, C.; Mulder, J. A.; Grebe, T. P. Org. Lett. 2002, 4, 2417. (d) Saito, N.; Sato, Y.; Mori, M. Org. Lett. 2002, 4, 803. With oxygen: (e) Clark, J. S.; Trevitt, G. P.; Boyall, D.; Stammen, B. Chem. Commun. 1998, 2629. (f) Clark, J. S.; Elustondo, F.; Trevitt, G. P.; Boyall, D.; Robertson, J.; Blake, A. J.; Wilson, C.; Stammen, B. Tetrahedron 2002, 58, 1973. (g) Schramm, M. P.; Reddy, D. S.; Kozmin, S. A. Angew. Chem., Int. Ed. 2001, 40, 4274. (h) Reddy, D. S.; Kozmin, S. A. J. Org. Chem. published online June 12, http://dx.doi.org/10.1021/jo049431g. With phosphorous: Schramm, M. P.; Reddy, D. S.; Kozmin, S. Angew. Chem., Int. Ed. 2002, 40, 4274. With phosphorus: (i) Timmer, M. S. M.; Ovaa, H.; Filippov, D. V.; van der Marel, G. A.; van Boom, J. H. Tetrahedron Lett. 2001, 42, 8231.
25. Other heteroatom-containing enyne RCM, see the following. With boron: (a) Micalizio, G.; Schreiber, S. L. Angew. Chem., Int. Ed. 2002, 41, 3272. (b) Renaud, J.; Graf, C.-D.; Oberer, L. Angew. Chem., Int. Ed. 2000, 39, 3101. With nitrogen: (c) Huang, J.; Xiong, H.; Hsung, R. P.; Rameshkumar, C.; Mulder, J. A.; Grebe, T. P. Org. Lett. 2002, 4, 2417. (d) Saito, N.; Sato, Y.; Mori, M. Org. Lett. 2002, 4, 803. With oxygen: (e) Clark, J. S.; Trevitt, G. P.; Boyall, D.; Stammen, B. Chem. Commun. 1998, 2629. (f) Clark, J. S.; Elustondo, F.; Trevitt, G. P.; Boyall, D.; Robertson, J.; Blake, A. J.; Wilson, C.; Stammen, B. Tetrahedron 2002, 58, 1973. (g) Schramm, M. P.; Reddy, D. S.; Kozmin, S. A. Angew. Chem., Int. Ed. 2001, 40, 4274. (h) Reddy, D. S.; Kozmin, S. A. J. Org. Chem. published online June 12, http://dx.doi.org/10.1021/jo049431g. With phosphorous: Schramm, M. P.; Reddy, D. S.; Kozmin, S. Angew. Chem., Int. Ed. 2002, 40, 4274. With phosphorus: (i) Timmer, M. S. M.; Ovaa, H.; Filippov, D. V.; van der Marel, G. A.; van Boom, J. H. Tetrahedron Lett. 2001, 42, 8231.
26. Other heteroatom-containing enyne RCM, see the following. With boron: (a) Micalizio, G.; Schreiber, S. L. Angew. Chem., Int. Ed. 2002, 41, 3272. (b) Renaud, J.; Graf, C.-D.; Oberer, L. Angew. Chem., Int. Ed. 2000, 39, 3101. With nitrogen: (c) Huang, J.; Xiong, H.; Hsung, R. P.; Rameshkumar, C.; Mulder, J. A.; Grebe, T. P. Org. Lett. 2002, 4, 2417. (d) Saito, N.; Sato, Y.; Mori, M. Org. Lett. 2002, 4, 803. With oxygen: (e) Clark, J. S.; Trevitt, G. P.; Boyall, D.; Stammen, B. Chem. Commun. 1998, 2629. (f) Clark, J. S.; Elustondo, F.; Trevitt, G. P.; Boyall, D.; Robertson, J.; Blake, A. J.; Wilson, C.; Stammen, B. Tetrahedron 2002, 58, 1973. (g) Schramm, M. P.; Reddy, D. S.; Kozmin, S. A. Angew. Chem., Int. Ed. 2001, 40, 4274. (h) Reddy, D. S.; Kozmin, S. A. J. Org. Chem. published online June 12, http://dx.doi.org/10.1021/jo049431g. With phosphorous: Schramm, M. P.; Reddy, D. S.; Kozmin, S. Angew. Chem., Int. Ed. 2002, 40, 4274. With phosphorus: (i) Timmer, M. S. M.; Ovaa, H.; Filippov, D. V.; van der Marel, G. A.; van Boom, J. H. Tetrahedron Lett. 2001, 42, 8231.
27. Other heteroatom-containing enyne RCM, see the following. With boron: (a) Micalizio, G.; Schreiber, S. L. Angew. Chem., Int. Ed. 2002, 41, 3272. (b) Renaud, J.; Graf, C.-D.; Oberer, L. Angew. Chem., Int. Ed. 2000, 39, 3101. With nitrogen: (c) Huang, J.; Xiong, H.; Hsung, R. P.; Rameshkumar, C.; Mulder, J. A.; Grebe, T. P. Org. Lett. 2002, 4, 2417. (d) Saito, N.; Sato, Y.; Mori, M. Org. Lett. 2002, 4, 803. With oxygen: (e) Clark, J. S.; Trevitt, G. P.; Boyall, D.; Stammen, B. Chem. Commun. 1998, 2629. (f) Clark, J. S.; Elustondo, F.; Trevitt, G. P.; Boyall, D.; Robertson, J.; Blake, A. J.; Wilson, C.; Stammen, B. Tetrahedron 2002, 58, 1973. (g) Schramm, M. P.; Reddy, D. S.; Kozmin, S. A. Angew. Chem., Int. Ed. 2001, 40, 4274. (h) Reddy, D. S.; Kozmin, S. A. J. Org. Chem. published online June 12, http://dx.doi.org/10.1021/jo049431g. With phosphorous: Schramm, M. P.; Reddy, D. S.; Kozmin, S. Angew. Chem., Int. Ed. 2002, 40, 4274. With phosphorus: (i) Timmer, M. S. M.; Ovaa, H.; Filippov, D. V.; van der Marel, G. A.; van Boom, J. H. Tetrahedron Lett. 2001, 42, 8231.
28. Other heteroatom-containing enyne RCM, see the following. With boron: (a) Micalizio, G.; Schreiber, S. L. Angew. Chem., Int. Ed. 2002, 41, 3272. (b) Renaud, J.; Graf, C.-D.; Oberer, L. Angew. Chem., Int. Ed. 2000, 39, 3101. With nitrogen: (c) Huang, J.; Xiong, H.; Hsung, R. P.; Rameshkumar, C.; Mulder, J. A.; Grebe, T. P. Org. Lett. 2002, 4, 2417. (d) Saito, N.; Sato, Y.; Mori, M. Org. Lett. 2002, 4, 803. With oxygen: (e) Clark, J. S.; Trevitt, G. P.; Boyall, D.; Stammen, B. Chem. Commun. 1998, 2629. (f) Clark, J. S.; Elustondo, F.; Trevitt, G. P.; Boyall, D.; Robertson, J.; Blake, A. J.; Wilson, C.; Stammen, B. Tetrahedron 2002, 58, 1973. (g) Schramm, M. P.; Reddy, D. S.; Kozmin, S. A. Angew. Chem., Int. Ed. 2001, 40, 4274. (h) Reddy, D. S.; Kozmin, S. A. J. Org. Chem. published online June 12, http://dx.doi.org/10.1021/jo049431g. With phosphorous: Schramm, M. P.; Reddy, D. S.; Kozmin, S. Angew. Chem., Int. Ed. 2002, 40, 4274. With phosphorus: (i) Timmer, M. S. M.; Ovaa, H.; Filippov, D. V.; van der Marel, G. A.; van Boom, J. H. Tetrahedron Lett. 2001, 42, 8231.
29. Other heteroatom-containing enyne RCM, see the following. With boron: (a) Micalizio, G.; Schreiber, S. L. Angew. Chem., Int. Ed. 2002, 41, 3272. (b) Renaud, J.; Graf, C.-D.; Oberer, L. Angew. Chem., Int. Ed. 2000, 39, 3101. With nitrogen: (c) Huang, J.; Xiong, H.; Hsung, R. P.; Rameshkumar, C.; Mulder, J. A.; Grebe, T. P. Org. Lett. 2002, 4, 2417. (d) Saito, N.; Sato, Y.; Mori, M. Org. Lett. 2002, 4, 803. With oxygen: (e) Clark, J. S.; Trevitt, G. P.; Boyall, D.; Stammen, B. Chem. Commun. 1998, 2629. (f) Clark, J. S.; Elustondo, F.; Trevitt, G. P.; Boyall, D.; Robertson, J.; Blake, A. J.; Wilson, C.; Stammen, B. Tetrahedron 2002, 58, 1973. (g) Schramm, M. P.; Reddy, D. S.; Kozmin, S. A. Angew. Chem., Int. Ed. 2001, 40, 4274. (h) Reddy, D. S.; Kozmin, S. A. J. Org. Chem. published online June 12, http://dx.doi.org/10.1021/jo049431g. With phosphorous: Schramm, M. P.; Reddy, D. S.; Kozmin, S. Angew. Chem., Int. Ed. 2002, 40, 4274. With phosphorus: (i) Timmer, M. S. M.; Ovaa, H.; Filippov, D. V.; van der Marel, G. A.; van Boom, J. H. Tetrahedron Lett. 2001, 42, 8231.
30. Other heteroatom-containing enyne RCM, see the following. With boron: (a) Micalizio, G.; Schreiber, S. L. Angew. Chem., Int. Ed. 2002, 41, 3272. (b) Renaud, J.; Graf, C.-D.; Oberer, L. Angew. Chem., Int. Ed. 2000, 39, 3101. With nitrogen: (c) Huang, J.; Xiong, H.; Hsung, R. P.; Rameshkumar, C.; Mulder, J. A.; Grebe, T. P. Org. Lett. 2002, 4, 2417. (d) Saito, N.; Sato, Y.; Mori, M. Org. Lett. 2002, 4, 803. With oxygen: (e) Clark, J. S.; Trevitt, G. P.; Boyall, D.; Stammen, B. Chem. Commun. 1998, 2629. (f) Clark, J. S.; Elustondo, F.; Trevitt, G. P.; Boyall, D.; Robertson, J.; Blake, A. J.; Wilson, C.; Stammen, B. Tetrahedron 2002, 58, 1973. (g) Schramm, M. P.; Reddy, D. S.; Kozmin, S. A. Angew. Chem., Int. Ed. 2001, 40, 4274. (h) Reddy, D. S.; Kozmin, S. A. J. Org. Chem. published online June 12, http://dx.doi.org/10.1021/jo049431g. With phosphorous: Schramm, M. P.; Reddy, D. S.; Kozmin, S. Angew. Chem., Int. Ed. 2002, 40, 4274. With phosphorus: (i) Timmer, M. S. M.; Ovaa, H.; Filippov, D. V.; van der Marel, G. A.; van Boom, J. H. Tetrahedron Lett. 2001, 42, 8231.
31. Other heteroatom-containing enyne RCM, see the following. With boron: (a) Micalizio, G.; Schreiber, S. L. Angew. Chem., Int. Ed. 2002, 41, 3272. (b) Renaud, J.; Graf, C.-D.; Oberer, L. Angew. Chem., Int. Ed. 2000, 39, 3101. With nitrogen: (c) Huang, J.; Xiong, H.; Hsung, R. P.; Rameshkumar, C.; Mulder, J. A.; Grebe, T. P. Org. Lett. 2002, 4, 2417. (d) Saito, N.; Sato, Y.; Mori, M. Org. Lett. 2002, 4, 803. With oxygen: (e) Clark, J. S.; Trevitt, G. P.; Boyall, D.; Stammen, B. Chem. Commun. 1998, 2629. (f) Clark, J. S.; Elustondo, F.; Trevitt, G. P.; Boyall, D.; Robertson, J.; Blake, A. J.; Wilson, C.; Stammen, B. Tetrahedron 2002, 58, 1973. (g) Schramm, M. P.; Reddy, D. S.; Kozmin, S. A. Angew. Chem., Int. Ed. 2001, 40, 4274. (h) Reddy, D. S.; Kozmin, S. A. J. Org. Chem. published online June 12, http://dx.doi.org/10.1021/jo049431g. With phosphorous: Schramm, M. P.; Reddy, D. S.; Kozmin, S. Angew. Chem., Int. Ed. 2002, 40, 4274. With phosphorus: (i) Timmer, M. S. M.; Ovaa, H.; Filippov, D. V.; van der Marel, G. A.; van Boom, J. H. Tetrahedron Lett. 2001, 42, 8231.
32. Other heteroatom-containing enyne RCM, see the following. With boron: (a) Micalizio, G.; Schreiber, S. L. Angew. Chem., Int. Ed. 2002, 41, 3272. (b) Renaud, J.; Graf, C.-D.; Oberer, L. Angew. Chem., Int. Ed. 2000, 39, 3101. With nitrogen: (c) Huang, J.; Xiong, H.; Hsung, R. P.; Rameshkumar, C.; Mulder, J. A.; Grebe, T. P. Org. Lett. 2002, 4, 2417. (d) Saito, N.; Sato, Y.; Mori, M. Org. Lett. 2002, 4, 803. With oxygen: (e) Clark, J. S.; Trevitt, G. P.; Boyall, D.; Stammen, B. Chem. Commun. 1998, 2629. (f) Clark, J. S.; Elustondo, F.; Trevitt, G. P.; Boyall, D.; Robertson, J.; Blake, A. J.; Wilson, C.; Stammen, B. Tetrahedron 2002, 58, 1973. (g) Schramm, M. P.; Reddy, D. S.; Kozmin, S. A. Angew. Chem., Int. Ed. 2001, 40, 4274. (h) Reddy, D. S.; Kozmin, S. A. J. Org. Chem. published online June 12, http://dx.doi.org/10.1021/jo049431g. With phosphorous: Schramm, M. P.; Reddy, D. S.; Kozmin, S. Angew. Chem., Int. Ed. 2002, 40, 4274. With phosphorus: (i) Timmer, M. S. M.; Ovaa, H.; Filippov, D. V.; van der Marel, G. A.; van Boom, J. H. Tetrahedron Lett. 2001, 42, 8231.
33. Kim, S.-H.; Zeurcher, W. J.; Bowden, N.; Grubbs, R. H. J. Org. Chem. 1996, 61, 1073.
34. Hansen, E. C.; Lee, D. J. Am. Chem. Soc. 2003, 125, 9582.
35. For an alternative method of making alkynylsilyl ethers see: Stork, G.; Keitz, P. F. Tetrahedron Lett. 1989, 30, 6981.
36. For the use of alkynylsilyloxy-tethered ene - ynes in other reactions, see: (a) Petit, M.; Chouraqui, G.; Aubert, C.; Malacria, M. Org. Lett. 2003, 5, 2037. (b) Chouraqui, G.; Petit, M.; Aubert, C.; Malacria, M. Org. Lett. 2004, 6, 1519.
37. For the use of alkynylsilyloxy-tethered ene - ynes in other reactions, see: (a) Petit, M.; Chouraqui, G.; Aubert, C.; Malacria, M. Org. Lett. 2003, 5, 2037. (b) Chouraqui, G.; Petit, M.; Aubert, C.; Malacria, M. Org. Lett. 2004, 6, 1519.
38. Reviews, see: (a) Denmark, S. E.; Sweis, R. F. Acc. Chem. Res. 2002, 35, 835. (b) Denmark, S. E.; Sweis, R. F. Chem. Pharm. Bull. 2002, 50, 1531. (c) Denmark, S. E.; Ober, M. H. Aldrichim. Acta 2003, 36, 75. For mechanistic studies, see: (d) Denmark, S. E.; Sweis, R. F.; Wehrli, D. J. Am. Chem. Soc. 2004, 126, 4865. (e) Denmark, S. E.; Sweis, R. F. J. Am. Chem. Soc. 2004, 126, 4876.
39. Reviews, see: (a) Denmark, S. E.; Sweis, R. F. Acc. Chem. Res. 2002, 35, 835. (b) Denmark, S. E.; Sweis, R. F. Chem. Pharm. Bull. 2002, 50, 1531. (c) Denmark, S. E.; Ober, M. H. Aldrichim. Acta 2003, 36, 75. For mechanistic studies, see: (d) Denmark, S. E.; Sweis, R. F.; Wehrli, D. J. Am. Chem. Soc. 2004, 126, 4865. (e) Denmark, S. E.; Sweis, R. F. J. Am. Chem. Soc. 2004, 126, 4876.
40. Reviews, see: (a) Denmark, S. E.; Sweis, R. F. Acc. Chem. Res. 2002, 35, 835. (b) Denmark, S. E.; Sweis, R. F. Chem. Pharm. Bull. 2002, 50, 1531. (c) Denmark, S. E.; Ober, M. H. Aldrichim. Acta 2003, 36, 75. For mechanistic studies, see: (d) Denmark, S. E.; Sweis, R. F.; Wehrli, D. J. Am. Chem. Soc. 2004, 126, 4865. (e) Denmark, S. E.; Sweis, R. F. J. Am. Chem. Soc. 2004, 126, 4876.
41. Reviews, see: (a) Denmark, S. E.; Sweis, R. F. Acc. Chem. Res. 2002, 35, 835. (b) Denmark, S. E.; Sweis, R. F. Chem. Pharm. Bull. 2002, 50, 1531. (c) Denmark, S. E.; Ober, M. H. Aldrichim. Acta 2003, 36, 75. For mechanistic studies, see: (d) Denmark, S. E.; Sweis, R. F.; Wehrli, D. J. Am. Chem. Soc. 2004, 126, 4865. (e) Denmark, S. E.; Sweis, R. F. J. Am. Chem. Soc. 2004, 126, 4876.
42. Reviews, see: (a) Denmark, S. E.; Sweis, R. F. Acc. Chem. Res. 2002, 35, 835. (b) Denmark, S. E.; Sweis, R. F. Chem. Pharm. Bull. 2002, 50, 1531. (c) Denmark, S. E.; Ober, M. H. Aldrichim. Acta 2003, 36, 75. For mechanistic studies, see: (d) Denmark, S. E.; Sweis, R. F.; Wehrli, D. J. Am. Chem. Soc. 2004, 126, 4865. (e) Denmark, S. E.; Sweis, R. F. J. Am. Chem. Soc. 2004, 126, 4876.
43. Examples of silyloxy-tethered diene RCM reactions, see: (a) Chang, S.; Grubbs, R. H. Tetrahedron Lett. 1997, 38, 4757. (b) Evans, P. A.; Murthy, S. J. Org. Chem. 1998, 63, 6768. (c) Hoye, T. R.; Promo, M. A. Tetrahedron Lett. 1999, 40, 1429. (d) Shu, S. S.; Cefalo, D. R.; La, D. S.; Jamieson, J. Y.; Davis, W. M.; Hoveyda, A. H.; Schrock, R. R. J. Am. Chem. Soc. 1999, 121, 8251. (e) Taylor, R. E.; Engelhardt, F. C.; Schmitt, M. J.; Yuan, H. J. Am. Chem. Soc. 2001, 123, 2964. (f) Kiely, A. F.; Jernelius, J. A.; Schrock, R. R.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 2868. (g) Van de Weghe, P.; Aoun, D.; Boiteau, J.-G.; Eustacbe, J. Org. Lett. 2002, 4, 4105. (h) Evans, P. A.; Cui, J.; Buffone, G. P. Angew. Chem., Int. Ed. 2003, 42, 1734. (i) Evans, P. A.; Cui, J.; Gharpure, S. J.; Polosukhin, A.; Zhang, H.-R. J. Am. Chem. Soc. 2003, 125, 14702.
44. Examples of silyloxy-tethered diene RCM reactions, see: (a) Chang, S.; Grubbs, R. H. Tetrahedron Lett. 1997, 38, 4757. (b) Evans, P. A.; Murthy, S. J. Org. Chem. 1998, 63, 6768. (c) Hoye, T. R.; Promo, M. A. Tetrahedron Lett. 1999, 40, 1429. (d) Shu, S. S.; Cefalo, D. R.; La, D. S.; Jamieson, J. Y.; Davis, W. M.; Hoveyda, A. H.; Schrock, R. R. J. Am. Chem. Soc. 1999, 121, 8251. (e) Taylor, R. E.; Engelhardt, F. C.; Schmitt, M. J.; Yuan, H. J. Am. Chem. Soc. 2001, 123, 2964. (f) Kiely, A. F.; Jernelius, J. A.; Schrock, R. R.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 2868. (g) Van de Weghe, P.; Aoun, D.; Boiteau, J.-G.; Eustacbe, J. Org. Lett. 2002, 4, 4105. (h) Evans, P. A.; Cui, J.; Buffone, G. P. Angew. Chem., Int. Ed. 2003, 42, 1734. (i) Evans, P. A.; Cui, J.; Gharpure, S. J.; Polosukhin, A.; Zhang, H.-R. J. Am. Chem. Soc. 2003, 125, 14702.
45. Examples of silyloxy-tethered diene RCM reactions, see: (a) Chang, S.; Grubbs, R. H. Tetrahedron Lett. 1997, 38, 4757. (b) Evans, P. A.; Murthy, S. J. Org. Chem. 1998, 63, 6768. (c) Hoye, T. R.; Promo, M. A. Tetrahedron Lett. 1999, 40, 1429. (d) Shu, S. S.; Cefalo, D. R.; La, D. S.; Jamieson, J. Y.; Davis, W. M.; Hoveyda, A. H.; Schrock, R. R. J. Am. Chem. Soc. 1999, 121, 8251. (e) Taylor, R. E.; Engelhardt, F. C.; Schmitt, M. J.; Yuan, H. J. Am. Chem. Soc. 2001, 123, 2964. (f) Kiely, A. F.; Jernelius, J. A.; Schrock, R. R.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 2868. (g) Van de Weghe, P.; Aoun, D.; Boiteau, J.-G.; Eustacbe, J. Org. Lett. 2002, 4, 4105. (h) Evans, P. A.; Cui, J.; Buffone, G. P. Angew. Chem., Int. Ed. 2003, 42, 1734. (i) Evans, P. A.; Cui, J.; Gharpure, S. J.; Polosukhin, A.; Zhang, H.-R. J. Am. Chem. Soc. 2003, 125, 14702.
46. Examples of silyloxy-tethered diene RCM reactions, see: (a) Chang, S.; Grubbs, R. H. Tetrahedron Lett. 1997, 38, 4757. (b) Evans, P. A.; Murthy, S. J. Org. Chem. 1998, 63, 6768. (c) Hoye, T. R.; Promo, M. A. Tetrahedron Lett. 1999, 40, 1429. (d) Shu, S. S.; Cefalo, D. R.; La, D. S.; Jamieson, J. Y.; Davis, W. M.; Hoveyda, A. H.; Schrock, R. R. J. Am. Chem. Soc. 1999, 121, 8251. (e) Taylor, R. E.; Engelhardt, F. C.; Schmitt, M. J.; Yuan, H. J. Am. Chem. Soc. 2001, 123, 2964. (f) Kiely, A. F.; Jernelius, J. A.; Schrock, R. R.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 2868. (g) Van de Weghe, P.; Aoun, D.; Boiteau, J.-G.; Eustacbe, J. Org. Lett. 2002, 4, 4105. (h) Evans, P. A.; Cui, J.; Buffone, G. P. Angew. Chem., Int. Ed. 2003, 42, 1734. (i) Evans, P. A.; Cui, J.; Gharpure, S. J.; Polosukhin, A.; Zhang, H.-R. J. Am. Chem. Soc. 2003, 125, 14702.
47. Examples of silyloxy-tethered diene RCM reactions, see: (a) Chang, S.; Grubbs, R. H. Tetrahedron Lett. 1997, 38, 4757. (b) Evans, P. A.; Murthy, S. J. Org. Chem. 1998, 63, 6768. (c) Hoye, T. R.; Promo, M. A. Tetrahedron Lett. 1999, 40, 1429. (d) Shu, S. S.; Cefalo, D. R.; La, D. S.; Jamieson, J. Y.; Davis, W. M.; Hoveyda, A. H.; Schrock, R. R. J. Am. Chem. Soc. 1999, 121, 8251. (e) Taylor, R. E.; Engelhardt, F. C.; Schmitt, M. J.; Yuan, H. J. Am. Chem. Soc. 2001, 123, 2964. (f) Kiely, A. F.; Jernelius, J. A.; Schrock, R. R.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 2868. (g) Van de Weghe, P.; Aoun, D.; Boiteau, J.-G.; Eustacbe, J. Org. Lett. 2002, 4, 4105. (h) Evans, P. A.; Cui, J.; Buffone, G. P. Angew. Chem., Int. Ed. 2003, 42, 1734. (i) Evans, P. A.; Cui, J.; Gharpure, S. J.; Polosukhin, A.; Zhang, H.-R. J. Am. Chem. Soc. 2003, 125, 14702.
48. Examples of silyloxy-tethered diene RCM reactions, see: (a) Chang, S.; Grubbs, R. H. Tetrahedron Lett. 1997, 38, 4757. (b) Evans, P. A.; Murthy, S. J. Org. Chem. 1998, 63, 6768. (c) Hoye, T. R.; Promo, M. A. Tetrahedron Lett. 1999, 40, 1429. (d) Shu, S. S.; Cefalo, D. R.; La, D. S.; Jamieson, J. Y.; Davis, W. M.; Hoveyda, A. H.; Schrock, R. R. J. Am. Chem. Soc. 1999, 121, 8251. (e) Taylor, R. E.; Engelhardt, F. C.; Schmitt, M. J.; Yuan, H. J. Am. Chem. Soc. 2001, 123, 2964. (f) Kiely, A. F.; Jernelius, J. A.; Schrock, R. R.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 2868. (g) Van de Weghe, P.; Aoun, D.; Boiteau, J.-G.; Eustacbe, J. Org. Lett. 2002, 4, 4105. (h) Evans, P. A.; Cui, J.; Buffone, G. P. Angew. Chem., Int. Ed. 2003, 42, 1734. (i) Evans, P. A.; Cui, J.; Gharpure, S. J.; Polosukhin, A.; Zhang, H.-R. J. Am. Chem. Soc. 2003, 125, 14702.
49. Examples of silyloxy-tethered diene RCM reactions, see: (a) Chang, S.; Grubbs, R. H. Tetrahedron Lett. 1997, 38, 4757. (b) Evans, P. A.; Murthy, S. J. Org. Chem. 1998, 63, 6768. (c) Hoye, T. R.; Promo, M. A. Tetrahedron Lett. 1999, 40, 1429. (d) Shu, S. S.; Cefalo, D. R.; La, D. S.; Jamieson, J. Y.; Davis, W. M.; Hoveyda, A. H.; Schrock, R. R. J. Am. Chem. Soc. 1999, 121, 8251. (e) Taylor, R. E.; Engelhardt, F. C.; Schmitt, M. J.; Yuan, H. J. Am. Chem. Soc. 2001, 123, 2964. (f) Kiely, A. F.; Jernelius, J. A.; Schrock, R. R.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 2868. (g) Van de Weghe, P.; Aoun, D.; Boiteau, J.-G.; Eustacbe, J. Org. Lett. 2002, 4, 4105. (h) Evans, P. A.; Cui, J.; Buffone, G. P. Angew. Chem., Int. Ed. 2003, 42, 1734. (i) Evans, P. A.; Cui, J.; Gharpure, S. J.; Polosukhin, A.; Zhang, H.-R. J. Am. Chem. Soc. 2003, 125, 14702.
50. Examples of silyloxy-tethered diene RCM reactions, see: (a) Chang, S.; Grubbs, R. H. Tetrahedron Lett. 1997, 38, 4757. (b) Evans, P. A.; Murthy, S. J. Org. Chem. 1998, 63, 6768. (c) Hoye, T. R.; Promo, M. A. Tetrahedron Lett. 1999, 40, 1429. (d) Shu, S. S.; Cefalo, D. R.; La, D. S.; Jamieson, J. Y.; Davis, W. M.; Hoveyda, A. H.; Schrock, R. R. J. Am. Chem. Soc. 1999, 121, 8251. (e) Taylor, R. E.; Engelhardt, F. C.; Schmitt, M. J.; Yuan, H. J. Am. Chem. Soc. 2001, 123, 2964. (f) Kiely, A. F.; Jernelius, J. A.; Schrock, R. R.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 2868. (g) Van de Weghe, P.; Aoun, D.; Boiteau, J.-G.; Eustacbe, J. Org. Lett. 2002, 4, 4105. (h) Evans, P. A.; Cui, J.; Buffone, G. P. Angew. Chem., Int. Ed. 2003, 42, 1734. (i) Evans, P. A.; Cui, J.; Gharpure, S. J.; Polosukhin, A.; Zhang, H.-R. J. Am. Chem. Soc. 2003, 125, 14702.
51. Examples of silyloxy-tethered diene RCM reactions, see: (a) Chang, S.; Grubbs, R. H. Tetrahedron Lett. 1997, 38, 4757. (b) Evans, P. A.; Murthy, S. J. Org. Chem. 1998, 63, 6768. (c) Hoye, T. R.; Promo, M. A. Tetrahedron Lett. 1999, 40, 1429. (d) Shu, S. S.; Cefalo, D. R.; La, D. S.; Jamieson, J. Y.; Davis, W. M.; Hoveyda, A. H.; Schrock, R. R. J. Am. Chem. Soc. 1999, 121, 8251. (e) Taylor, R. E.; Engelhardt, F. C.; Schmitt, M. J.; Yuan, H. J. Am. Chem. Soc. 2001, 123, 2964. (f) Kiely, A. F.; Jernelius, J. A.; Schrock, R. R.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 2868. (g) Van de Weghe, P.; Aoun, D.; Boiteau, J.-G.; Eustacbe, J. Org. Lett. 2002, 4, 4105. (h) Evans, P. A.; Cui, J.; Buffone, G. P. Angew. Chem., Int. Ed. 2003, 42, 1734. (i) Evans, P. A.; Cui, J.; Gharpure, S. J.; Polosukhin, A.; Zhang, H.-R. J. Am. Chem. Soc. 2003, 125, 14702.
52. Examples of silyloxy-tethered enyne RCM, see: (a) Semeril, D.; Cleran, M.; Bruneau, C.; Dixneuf, P. H. Adv. Synth. Catal. 2001, 343, 184. (b) Yao, Q. Org. Lett. 2001, 3, 2069. (c) Semeril, D.; Cleran, M.; Perez, A. J.; Bruneau, C.; Dixneuf, P. H. J. Mol. Catal. A. 2002, 190, 9.
53. Examples of silyloxy-tethered enyne RCM, see: (a) Semeril, D.; Cleran, M.; Bruneau, C.; Dixneuf, P. H. Adv. Synth. Catal. 2001, 343, 184. (b) Yao, Q. Org. Lett. 2001, 3, 2069. (c) Semeril, D.; Cleran, M.; Perez, A. J.; Bruneau, C.; Dixneuf, P. H. J. Mol. Catal. A. 2002, 190, 9.
54. Examples of silyloxy-tethered enyne RCM, see: (a) Semeril, D.; Cleran, M.; Bruneau, C.; Dixneuf, P. H. Adv. Synth. Catal. 2001, 343, 184. (b) Yao, Q. Org. Lett. 2001, 3, 2069. (c) Semeril, D.; Cleran, M.; Perez, A. J.; Bruneau, C.; Dixneuf, P. H. J. Mol. Catal. A. 2002, 190, 9.
55. For general reviews on silicon tether, see: (a) Bols, M.; Skrydstrup, T. Chem. Rev. 1995, 95, 1253. (b) Fensterbank, L.; Malacria, M.; Sieburth, S. McN. Synthesis 1997, 813. (c) Gauthier, D. R., Jr.; Zandi, K. S.; Shea, K. J. Tetrahedron 1998, 54, 2290.
56. For general reviews on silicon tether, see: (a) Bols, M.; Skrydstrup, T. Chem. Rev. 1995, 95, 1253. (b) Fensterbank, L.; Malacria, M.; Sieburth, S. McN. Synthesis 1997, 813. (c) Gauthier, D. R., Jr.; Zandi, K. S.; Shea, K. J. Tetrahedron 1998, 54, 2290.
57. For general reviews on silicon tether, see: (a) Bols, M.; Skrydstrup, T. Chem. Rev. 1995, 95, 1253. (b) Fensterbank, L.; Malacria, M.; Sieburth, S. McN. Synthesis 1997, 813. (c) Gauthier, D. R., Jr.; Zandi, K. S.; Shea, K. J. Tetrahedron 1998, 54, 2290.
58. Synthesis of related siloxacycles by ruthenium-catalyzed intramolecular hydrosilylation, see: Trost, B. M.; Ball. Z. T. J. Am. Chem. Soc. 2003, 125, 30.
59. (a) Ojima, I.; Kogure, T.; Nihonyangi, M.; Kono, H.; Inaba, S. Chem. Lett. 1973, 501.
60. (b) Luo, X.-L.; Crabtree, R. H. J. Am. Chem. Soc. 1989, 111, 2527.
61. (c) Yamamoto, K.; Takemae, M. Bull. Chem. Soc. Jpn. 1989, 62, 2111.
62. (d) Doyle, M. P.; High, K. G.; Bagheri, V.; Pieters, R. J.; Lewis, P. J.; Pearson, M. M. J. Org. Chem. 1990, 55, 6082.
63. (e) Maifeld, S. V.; Miller, R. L.; Lee, D. Tetrahedron Lett. 2002, 43, 6363.
64. 2, 3-butyn-1-ol (entry 10 in Table 1) undergoes preferential C-silylation, see: Na, Y.; Chang, S. Org. Lett. 2000, 2, 1887. For a review of solvent free reactions, see: (c) Tanaka, K.; Toda, F. Chem. Rev. 2000, 100, 1025.
65. 2, 3-butyn-1-ol (entry 10 in Table 1) undergoes preferential C-silylation, see: Na, Y.; Chang, S. Org. Lett. 2000, 2, 1887. For a review of solvent free reactions, see: (c) Tanaka, K.; Toda, F. Chem. Rev. 2000, 100, 1025.
66. 2, 3-butyn-1-ol (entry 10 in Table 1) undergoes preferential C-silylation, see: Na, Y.; Chang, S. Org. Lett. 2000, 2, 1887. For a review of solvent free reactions, see: (c) Tanaka, K.; Toda, F. Chem. Rev. 2000, 100, 1025.
67. When entry 5 in Table 1 was repeated with 5.0 g (32.8 mmol) of myrtenol, 8.16 g (93% yield) of the corresponding silyl ether was obtained.
68. (a) Beesely, R. M.; Ingold, C. K.; Thorpe, J. F. J. Chem. Soc. 1915, 107, 1080.
69. (b) Lightstone, F. C.; Bruice, T. C. J. Am. Chem. Soc. 1994, 116, 10789 and references therein.