Diastereoselective temporary silicon-tethered ring-closing-metathesis reactions with prochiral alcohols: A new approach to long-range asymmetric induction

Angewandte Chemie - International Edition

Volumn 42, Issue 15, 2003, Pages 1734-1737

  Evans, P Andrew ^a   Cui, Jian ^a   Buffone, Gerald P ^b  

^a INDIANA UNIVERSITY   (United States)

^b UNIVERSITY OF DELAWARE   (United States)

Author keywords

Cyclization; Diastereoselectivity; Medium sized rings; Metathesis; Silicon

Indexed keywords

ISOMERS; SILICON;

ASYMMETRIC INDUCTION;

STEREOCHEMISTRY;

ALCOHOL; DICHLOROMETHANE; SILICON;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHIRALITY; CIS TRANS ISOMERISM; CYCLIZATION; DIASTEREOISOMER; RING CLOSING METATHESIS; STEREOCHEMISTRY;

ALCOHOLS; CATALYSIS; CYCLIZATION; HETEROCYCLIC COMPOUNDS, 1-RING; KINETICS; SILANES; SILICON; STEREOISOMERISM;

EID: 0037879286     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200250486     Document Type: Article

References (42)

1. For recent reviews on long-range asymmetric induction, see: a) H. Sailes, A. Whiting, J. Chem. Soc. Perkin Trans. 1 2000, 1785-1805; b) K. Mikami, M. Shimizu, H.-C. Zhang, B. E. Maryanoff, Tetrahedron 2001, 57, 2917-2951, and references therein.
2. For recent reviews on long-range asymmetric induction, see: a) H. Sailes, A. Whiting, J. Chem. Soc. Perkin Trans. 1 2000, 1785-1805; b) K. Mikami, M. Shimizu, H.-C. Zhang, B. E. Maryanoff, Tetrahedron 2001, 57, 2917-2951, and references therein.
3. For recent examples of long-range asymmetric induction, see: a) M. Date, Y. Tamai, T. Hattori, H. Takayama, Y. Kamikubo, S. Miyano, J. Chem. Soc. Perkin Trans. 1 2001, 645-653; b) R. D. A. Hudson, C. E. Anson, M. F. Mahon, G. R. Stephenson, J. Organomet. Chem. 2001, 630, 88-103; c) S. J. O'Malley, J. L. Leighton, Angew. Chem. 2001, 113, 2999-3001; Angew. Chem. Int. Ed. 2001, 40, 2915-2917; d) M. W. Carson, G. Kim, S. J. Danishefsky, Angew. Chem. 2001, 113, 4585-4588; Angew. Chem. Int. Ed. 2001, 40, 4453-4456; d) E. M. Flamme, W. R. Roush, J. Am. Chem. Soc. 2002, 124, 13644-13645, and references therein.
4. For recent examples of long-range asymmetric induction, see: a) M. Date, Y. Tamai, T. Hattori, H. Takayama, Y. Kamikubo, S. Miyano, J. Chem. Soc. Perkin Trans. 1 2001, 645-653; b) R. D. A. Hudson, C. E. Anson, M. F. Mahon, G. R. Stephenson, J. Organomet. Chem. 2001, 630, 88-103; c) S. J. O'Malley, J. L. Leighton, Angew. Chem. 2001, 113, 2999-3001; Angew. Chem. Int. Ed. 2001, 40, 2915-2917; d) M. W. Carson, G. Kim, S. J. Danishefsky, Angew. Chem. 2001, 113, 4585-4588; Angew. Chem. Int. Ed. 2001, 40, 4453-4456; d) E. M. Flamme, W. R. Roush, J. Am. Chem. Soc. 2002, 124, 13644-13645, and references therein.
5. For recent examples of long-range asymmetric induction, see: a) M. Date, Y. Tamai, T. Hattori, H. Takayama, Y. Kamikubo, S. Miyano, J. Chem. Soc. Perkin Trans. 1 2001, 645-653; b) R. D. A. Hudson, C. E. Anson, M. F. Mahon, G. R. Stephenson, J. Organomet. Chem. 2001, 630, 88-103; c) S. J. O'Malley, J. L. Leighton, Angew. Chem. 2001, 113, 2999-3001; Angew. Chem. Int. Ed. 2001, 40, 2915-2917; d) M. W. Carson, G. Kim, S. J. Danishefsky, Angew. Chem. 2001, 113, 4585-4588; Angew. Chem. Int. Ed. 2001, 40, 4453-4456; d) E. M. Flamme, W. R. Roush, J. Am. Chem. Soc. 2002, 124, 13644-13645, and references therein.
6. For recent examples of long-range asymmetric induction, see: a) M. Date, Y. Tamai, T. Hattori, H. Takayama, Y. Kamikubo, S. Miyano, J. Chem. Soc. Perkin Trans. 1 2001, 645-653; b) R. D. A. Hudson, C. E. Anson, M. F. Mahon, G. R. Stephenson, J. Organomet. Chem. 2001, 630, 88-103; c) S. J. O'Malley, J. L. Leighton, Angew. Chem. 2001, 113, 2999-3001; Angew. Chem. Int. Ed. 2001, 40, 2915-2917; d) M. W. Carson, G. Kim, S. J. Danishefsky, Angew. Chem. 2001, 113, 4585-4588; Angew. Chem. Int. Ed. 2001, 40, 4453-4456; d) E. M. Flamme, W. R. Roush, J. Am. Chem. Soc. 2002, 124, 13644-13645, and references therein.
7. For recent examples of long-range asymmetric induction, see: a) M. Date, Y. Tamai, T. Hattori, H. Takayama, Y. Kamikubo, S. Miyano, J. Chem. Soc. Perkin Trans. 1 2001, 645-653; b) R. D. A. Hudson, C. E. Anson, M. F. Mahon, G. R. Stephenson, J. Organomet. Chem. 2001, 630, 88-103; c) S. J. O'Malley, J. L. Leighton, Angew. Chem. 2001, 113, 2999-3001; Angew. Chem. Int. Ed. 2001, 40, 2915-2917; d) M. W. Carson, G. Kim, S. J. Danishefsky, Angew. Chem. 2001, 113, 4585-4588; Angew. Chem. Int. Ed. 2001, 40, 4453-4456; d) E. M. Flamme, W. R. Roush, J. Am. Chem. Soc. 2002, 124, 13644-13645, and references therein.
8. For recent examples of long-range asymmetric induction, see: a) M. Date, Y. Tamai, T. Hattori, H. Takayama, Y. Kamikubo, S. Miyano, J. Chem. Soc. Perkin Trans. 1 2001, 645-653; b) R. D. A. Hudson, C. E. Anson, M. F. Mahon, G. R. Stephenson, J. Organomet. Chem. 2001, 630, 88-103; c) S. J. O'Malley, J. L. Leighton, Angew. Chem. 2001, 113, 2999-3001; Angew. Chem. Int. Ed. 2001, 40, 2915-2917; d) M. W. Carson, G. Kim, S. J. Danishefsky, Angew. Chem. 2001, 113, 4585-4588; Angew. Chem. Int. Ed. 2001, 40, 4453-4456; d) E. M. Flamme, W. R. Roush, J. Am. Chem. Soc. 2002, 124, 13644-13645, and references therein.
9. For recent examples of long-range asymmetric induction, see: a) M. Date, Y. Tamai, T. Hattori, H. Takayama, Y. Kamikubo, S. Miyano, J. Chem. Soc. Perkin Trans. 1 2001, 645-653; b) R. D. A. Hudson, C. E. Anson, M. F. Mahon, G. R. Stephenson, J. Organomet. Chem. 2001, 630, 88-103; c) S. J. O'Malley, J. L. Leighton, Angew. Chem. 2001, 113, 2999-3001; Angew. Chem. Int. Ed. 2001, 40, 2915-2917; d) M. W. Carson, G. Kim, S. J. Danishefsky, Angew. Chem. 2001, 113, 4585-4588; Angew. Chem. Int. Ed. 2001, 40, 4453-4456; d) E. M. Flamme, W. R. Roush, J. Am. Chem. Soc. 2002, 124, 13644-13645, and references therein.
10. For recent reviews on ring-closing metathesis, see: a) R. H. Grubbs, S. Chang, Tetrahedron 1998, 54, 4413-4450; b) U. K. Pandit, H. S. Overkleeft, B. C. Borer, H. Bieräugel, Eur. J. Org. Chem. 1999, 959-968; c) A. Fürstner, Angew. Chem. 2000, 112, 3140-3172; Angew. Chem. Int. Ed. 2000, 39, 3012-3043, and references therein.
11. For recent reviews on ring-closing metathesis, see: a) R. H. Grubbs, S. Chang, Tetrahedron 1998, 54, 4413-4450; b) U. K. Pandit, H. S. Overkleeft, B. C. Borer, H. Bieräugel, Eur. J. Org. Chem. 1999, 959-968; c) A. Fürstner, Angew. Chem. 2000, 112, 3140-3172; Angew. Chem. Int. Ed. 2000, 39, 3012-3043, and references therein.
12. For recent reviews on ring-closing metathesis, see: a) R. H. Grubbs, S. Chang, Tetrahedron 1998, 54, 4413-4450; b) U. K. Pandit, H. S. Overkleeft, B. C. Borer, H. Bieräugel, Eur. J. Org. Chem. 1999, 959-968; c) A. Fürstner, Angew. Chem. 2000, 112, 3140-3172; Angew. Chem. Int. Ed. 2000, 39, 3012-3043, and references therein.
13. For recent reviews on ring-closing metathesis, see: a) R. H. Grubbs, S. Chang, Tetrahedron 1998, 54, 4413-4450; b) U. K. Pandit, H. S. Overkleeft, B. C. Borer, H. Bieräugel, Eur. J. Org. Chem. 1999, 959-968; c) A. Fürstner, Angew. Chem. 2000, 112, 3140-3172; Angew. Chem. Int. Ed. 2000, 39, 3012-3043, and references therein.
14. G. C. Fu, R. H. Grubbs, J. Am. Chem. Soc. 1992, 114, 5426-5427.
15. 2-symmetrical 1,4-diols, see: a) P. A. Evans, V. S. Murthy, J. Org. Chem. 1998, 63, 6768-6769; b) M. Lobbel, P. Köll, Tetrahedron: Asymmetry 2000, 11, 393-396.
16. 2-symmetrical 1,4-diols, see: a) P. A. Evans, V. S. Murthy, J. Org. Chem. 1998, 63, 6768-6769; b) M. Lobbel, P. Köll, Tetrahedron: Asymmetry 2000, 11, 393-396.
17. For examples of silicon-tethered ring-closing-metathesis cross-coupling reactions, see: a) T. R. Hoye, M. A. Promo, Tetrahedron Lett. 1999, 40, 1429-1432; b) J.-G. Boiteau, P. Van de -Weghe, J. Eustache, Tetrahedron Lett. 2001, 42, 239-242; c) B. A. Harrison, G. L. Verdine, Org. Lett. 2001, 3, 2157-2159.
18. For examples of silicon-tethered ring-closing-metathesis cross-coupling reactions, see: a) T. R. Hoye, M. A. Promo, Tetrahedron Lett. 1999, 40, 1429-1432; b) J.-G. Boiteau, P. Van de-Weghe, J. Eustache, Tetrahedron Lett. 2001, 42, 239-242; c) B. A. Harrison, G. L. Verdine, Org. Lett. 2001, 3, 2157-2159.
19. For examples of silicon-tethered ring-closing-metathesis cross-coupling reactions, see: a) T. R. Hoye, M. A. Promo, Tetrahedron Lett. 1999, 40, 1429-1432; b) J.-G. Boiteau, P. Van de -Weghe, J. Eustache, Tetrahedron Lett. 2001, 42, 239-242; c) B. A. Harrison, G. L. Verdine, Org. Lett. 2001, 3, 2157-2159.
20. For a related example of an enantioselective RCM using a prochiral alcohol, see: A. F. Kiely, J. A. Jernelius, R. R. Schrock, A. H. Hoveyda, J. Am. Chem. Soc. 2002, 124, 2868-2869.
21. For examples of diastereoselective ring-closing-metathesis reactions, see: a) C. M. Huwe, J. Velder, S. Blechert, Angew. Chem. 1996, 108, 2542-2544; Angew. Chem. Int. Ed. Engl. 1996, 35, 2376-2378; b) S. D. Burke, M. Müller, C. M. Beaudry, Org. Lett. 1999, 1, 1827-1829; c) H. Oguri, S.-Y. Sasaki, T. Oishi, M. Hirama, Tetrahedron Lett. 1999, 40, 5405-5408; d) M. Lautens, G. Hughes, Angew. Chem. 1999, 111, 160-162; Angew. Chem. Int. Ed. 1999, 38, 129-131; e) G. C. Lloyd-Jones, M. Murray, R. A. Stentiford, P. A. Worthington, Eur. J. Org. Chem. 2000, 975-985; f) D. J. Wallace, C. J. Cowden, D. J. Kennedy, M. S. Ashwood, I. F. Cottrell, U.-H. Dolling, Tetrahedron Lett. 2000, 41, 2027-2029; g) B. Schmidt, M. Westhus, Tetrahedron 2000, 56, 2421-2426; h) D. S. Stoianova, P. R. Hanson, Org. Lett. 2000, 2, 1769-1772; i) Y. Fukuda, H. Sasaki, M. Shindo, K. Shishido, Tetrahedron Lett. 2002, 43, 2047-2049; j) M. Ogasawara, T. Nagano, T. Hayashi, J. Am. Chem. Soc. 2002, 124, 9068-9069.
22. For examples of diastereoselective ring-closing-metathesis reactions, see: a) C. M. Huwe, J. Velder, S. Blechert, Angew. Chem. 1996, 108, 2542-2544; Angew. Chem. Int. Ed. Engl. 1996, 35, 2376-2378; b) S. D. Burke, M. Müller, C. M. Beaudry, Org. Lett. 1999, 1, 1827-1829; c) H. Oguri, S.-Y. Sasaki, T. Oishi, M. Hirama, Tetrahedron Lett. 1999, 40, 5405-5408; d) M. Lautens, G. Hughes, Angew. Chem. 1999, 111, 160-162; Angew. Chem. Int. Ed. 1999, 38, 129-131; e) G. C. Lloyd-Jones, M. Murray, R. A. Stentiford, P. A. Worthington, Eur. J. Org. Chem. 2000, 975-985; f) D. J. Wallace, C. J. Cowden, D. J. Kennedy, M. S. Ashwood, I. F. Cottrell, U.-H. Dolling, Tetrahedron Lett. 2000, 41, 2027-2029; g) B. Schmidt, M. Westhus, Tetrahedron 2000, 56, 2421-2426; h) D. S. Stoianova, P. R. Hanson, Org. Lett. 2000, 2, 1769-1772; i) Y. Fukuda, H. Sasaki, M. Shindo, K. Shishido, Tetrahedron Lett. 2002, 43, 2047-2049; j) M. Ogasawara, T. Nagano, T. Hayashi, J. Am. Chem. Soc. 2002, 124, 9068-9069.
23. For examples of diastereoselective ring-closing-metathesis reactions, see: a) C. M. Huwe, J. Velder, S. Blechert, Angew. Chem. 1996, 108, 2542-2544; Angew. Chem. Int. Ed. Engl. 1996, 35, 2376-2378; b) S. D. Burke, M. Müller, C. M. Beaudry, Org. Lett. 1999, 1, 1827-1829; c) H. Oguri, S.-Y. Sasaki, T. Oishi, M. Hirama, Tetrahedron Lett. 1999, 40, 5405-5408; d) M. Lautens, G. Hughes, Angew. Chem. 1999, 111, 160-162; Angew. Chem. Int. Ed. 1999, 38, 129-131; e) G. C. Lloyd-Jones, M. Murray, R. A. Stentiford, P. A. Worthington, Eur. J. Org. Chem. 2000, 975-985; f) D. J. Wallace, C. J. Cowden, D. J. Kennedy, M. S. Ashwood, I. F. Cottrell, U.-H. Dolling, Tetrahedron Lett. 2000, 41, 2027-2029; g) B. Schmidt, M. Westhus, Tetrahedron 2000, 56, 2421-2426; h) D. S. Stoianova, P. R. Hanson, Org. Lett. 2000, 2, 1769-1772; i) Y. Fukuda, H. Sasaki, M. Shindo, K. Shishido, Tetrahedron Lett. 2002, 43, 2047-2049; j) M. Ogasawara, T. Nagano, T. Hayashi, J. Am. Chem. Soc. 2002, 124, 9068-9069.
24. For examples of diastereoselective ring-closing-metathesis reactions, see: a) C. M. Huwe, J. Velder, S. Blechert, Angew. Chem. 1996, 108, 2542-2544; Angew. Chem. Int. Ed. Engl. 1996, 35, 2376-2378; b) S. D. Burke, M. Müller, C. M. Beaudry, Org. Lett. 1999, 1, 1827-1829; c) H. Oguri, S.-Y. Sasaki, T. Oishi, M. Hirama, Tetrahedron Lett. 1999, 40, 5405-5408; d) M. Lautens, G. Hughes, Angew. Chem. 1999, 111, 160-162; Angew. Chem. Int. Ed. 1999, 38, 129-131; e) G. C. Lloyd-Jones, M. Murray, R. A. Stentiford, P. A. Worthington, Eur. J. Org. Chem. 2000, 975-985; f) D. J. Wallace, C. J. Cowden, D. J. Kennedy, M. S. Ashwood, I. F. Cottrell, U.-H. Dolling, Tetrahedron Lett. 2000, 41, 2027-2029; g) B. Schmidt, M. Westhus, Tetrahedron 2000, 56, 2421-2426; h) D. S. Stoianova, P. R. Hanson, Org. Lett. 2000, 2, 1769-1772; i) Y. Fukuda, H. Sasaki, M. Shindo, K. Shishido, Tetrahedron Lett. 2002, 43, 2047-2049; j) M. Ogasawara, T. Nagano, T. Hayashi, J. Am. Chem. Soc. 2002, 124, 9068-9069.
25. For examples of diastereoselective ring-closing-metathesis reactions, see: a) C. M. Huwe, J. Velder, S. Blechert, Angew. Chem. 1996, 108, 2542-2544; Angew. Chem. Int. Ed. Engl. 1996, 35, 2376-2378; b) S. D. Burke, M. Müller, C. M. Beaudry, Org. Lett. 1999, 1, 1827-1829; c) H. Oguri, S.-Y. Sasaki, T. Oishi, M. Hirama, Tetrahedron Lett. 1999, 40, 5405-5408; d) M. Lautens, G. Hughes, Angew. Chem. 1999, 111, 160-162; Angew. Chem. Int. Ed. 1999, 38, 129-131; e) G. C. Lloyd-Jones, M. Murray, R. A. Stentiford, P. A. Worthington, Eur. J. Org. Chem. 2000, 975-985; f) D. J. Wallace, C. J. Cowden, D. J. Kennedy, M. S. Ashwood, I. F. Cottrell, U.-H. Dolling, Tetrahedron Lett. 2000, 41, 2027-2029; g) B. Schmidt, M. Westhus, Tetrahedron 2000, 56, 2421-2426; h) D. S. Stoianova, P. R. Hanson, Org. Lett. 2000, 2, 1769-1772; i) Y. Fukuda, H. Sasaki, M. Shindo, K. Shishido, Tetrahedron Lett. 2002, 43, 2047-2049; j) M. Ogasawara, T. Nagano, T. Hayashi, J. Am. Chem. Soc. 2002, 124, 9068-9069.
26. For examples of diastereoselective ring-closing-metathesis reactions, see: a) C. M. Huwe, J. Velder, S. Blechert, Angew. Chem. 1996, 108, 2542-2544; Angew. Chem. Int. Ed. Engl. 1996, 35, 2376-2378; b) S. D. Burke, M. Müller, C. M. Beaudry, Org. Lett. 1999, 1, 1827-1829; c) H. Oguri, S.-Y. Sasaki, T. Oishi, M. Hirama, Tetrahedron Lett. 1999, 40, 5405-5408; d) M. Lautens, G. Hughes, Angew. Chem. 1999, 111, 160-162; Angew. Chem. Int. Ed. 1999, 38, 129-131; e) G. C. Lloyd-Jones, M. Murray, R. A. Stentiford, P. A. Worthington, Eur. J. Org. Chem. 2000, 975-985; f) D. J. Wallace, C. J. Cowden, D. J. Kennedy, M. S. Ashwood, I. F. Cottrell, U.-H. Dolling, Tetrahedron Lett. 2000, 41, 2027-2029; g) B. Schmidt, M. Westhus, Tetrahedron 2000, 56, 2421-2426; h) D. S. Stoianova, P. R. Hanson, Org. Lett. 2000, 2, 1769-1772; i) Y. Fukuda, H. Sasaki, M. Shindo, K. Shishido, Tetrahedron Lett. 2002, 43, 2047-2049; j) M. Ogasawara, T. Nagano, T. Hayashi, J. Am. Chem. Soc. 2002, 124, 9068-9069.
27. For examples of diastereoselective ring-closing-metathesis reactions, see: a) C. M. Huwe, J. Velder, S. Blechert, Angew. Chem. 1996, 108, 2542-2544; Angew. Chem. Int. Ed. Engl. 1996, 35, 2376-2378; b) S. D. Burke, M. Müller, C. M. Beaudry, Org. Lett. 1999, 1, 1827-1829; c) H. Oguri, S.-Y. Sasaki, T. Oishi, M. Hirama, Tetrahedron Lett. 1999, 40, 5405-5408; d) M. Lautens, G. Hughes, Angew. Chem. 1999, 111, 160-162; Angew. Chem. Int. Ed. 1999, 38, 129-131; e) G. C. Lloyd-Jones, M. Murray, R. A. Stentiford, P. A. Worthington, Eur. J. Org. Chem. 2000, 975-985; f) D. J. Wallace, C. J. Cowden, D. J. Kennedy, M. S. Ashwood, I. F. Cottrell, U.-H. Dolling, Tetrahedron Lett. 2000, 41, 2027-2029; g) B. Schmidt, M. Westhus, Tetrahedron 2000, 56, 2421-2426; h) D. S. Stoianova, P. R. Hanson, Org. Lett. 2000, 2, 1769-1772; i) Y. Fukuda, H. Sasaki, M. Shindo, K. Shishido, Tetrahedron Lett. 2002, 43, 2047-2049; j) M. Ogasawara, T. Nagano, T. Hayashi, J. Am. Chem. Soc. 2002, 124, 9068-9069.
28. For examples of diastereoselective ring-closing-metathesis reactions, see: a) C. M. Huwe, J. Velder, S. Blechert, Angew. Chem. 1996, 108, 2542-2544; Angew. Chem. Int. Ed. Engl. 1996, 35, 2376-2378; b) S. D. Burke, M. Müller, C. M. Beaudry, Org. Lett. 1999, 1, 1827-1829; c) H. Oguri, S.-Y. Sasaki, T. Oishi, M. Hirama, Tetrahedron Lett. 1999, 40, 5405-5408; d) M. Lautens, G. Hughes, Angew. Chem. 1999, 111, 160-162; Angew. Chem. Int. Ed. 1999, 38, 129-131; e) G. C. Lloyd-Jones, M. Murray, R. A. Stentiford, P. A. Worthington, Eur. J. Org. Chem. 2000, 975-985; f) D. J. Wallace, C. J. Cowden, D. J. Kennedy, M. S. Ashwood, I. F. Cottrell, U.-H. Dolling, Tetrahedron Lett. 2000, 41, 2027-2029; g) B. Schmidt, M. Westhus, Tetrahedron 2000, 56, 2421-2426; h) D. S. Stoianova, P. R. Hanson, Org. Lett. 2000, 2, 1769-1772; i) Y. Fukuda, H. Sasaki, M. Shindo, K. Shishido, Tetrahedron Lett. 2002, 43, 2047-2049; j) M. Ogasawara, T. Nagano, T. Hayashi, J. Am. Chem. Soc. 2002, 124, 9068-9069.
29. For examples of diastereoselective ring-closing-metathesis reactions, see: a) C. M. Huwe, J. Velder, S. Blechert, Angew. Chem. 1996, 108, 2542-2544; Angew. Chem. Int. Ed. Engl. 1996, 35, 2376-2378; b) S. D. Burke, M. Müller, C. M. Beaudry, Org. Lett. 1999, 1, 1827-1829; c) H. Oguri, S.-Y. Sasaki, T. Oishi, M. Hirama, Tetrahedron Lett. 1999, 40, 5405-5408; d) M. Lautens, G. Hughes, Angew. Chem. 1999, 111, 160-162; Angew. Chem. Int. Ed. 1999, 38, 129-131; e) G. C. Lloyd-Jones, M. Murray, R. A. Stentiford, P. A. Worthington, Eur. J. Org. Chem. 2000, 975-985; f) D. J. Wallace, C. J. Cowden, D. J. Kennedy, M. S. Ashwood, I. F. Cottrell, U.-H. Dolling, Tetrahedron Lett. 2000, 41, 2027-2029; g) B. Schmidt, M. Westhus, Tetrahedron 2000, 56, 2421-2426; h) D. S. Stoianova, P. R. Hanson, Org. Lett. 2000, 2, 1769-1772; i) Y. Fukuda, H. Sasaki, M. Shindo, K. Shishido, Tetrahedron Lett. 2002, 43, 2047-2049; j) M. Ogasawara, T. Nagano, T. Hayashi, J. Am. Chem. Soc. 2002, 124, 9068-9069.
30. For examples of diastereoselective ring-closing-metathesis reactions, see: a) C. M. Huwe, J. Velder, S. Blechert, Angew. Chem. 1996, 108, 2542-2544; Angew. Chem. Int. Ed. Engl. 1996, 35, 2376-2378; b) S. D. Burke, M. Müller, C. M. Beaudry, Org. Lett. 1999, 1, 1827-1829; c) H. Oguri, S.-Y. Sasaki, T. Oishi, M. Hirama, Tetrahedron Lett. 1999, 40, 5405-5408; d) M. Lautens, G. Hughes, Angew. Chem. 1999, 111, 160-162; Angew. Chem. Int. Ed. 1999, 38, 129-131; e) G. C. Lloyd-Jones, M. Murray, R. A. Stentiford, P. A. Worthington, Eur. J. Org. Chem. 2000, 975-985; f) D. J. Wallace, C. J. Cowden, D. J. Kennedy, M. S. Ashwood, I. F. Cottrell, U.-H. Dolling, Tetrahedron Lett. 2000, 41, 2027-2029; g) B. Schmidt, M. Westhus, Tetrahedron 2000, 56, 2421-2426; h) D. S. Stoianova, P. R. Hanson, Org. Lett. 2000, 2, 1769-1772; i) Y. Fukuda, H. Sasaki, M. Shindo, K. Shishido, Tetrahedron Lett. 2002, 43, 2047-2049; j) M. Ogasawara, T. Nagano, T. Hayashi, J. Am. Chem. Soc. 2002, 124, 9068-9069.
31. For examples of diastereoselective ring-closing-metathesis reactions, see: a) C. M. Huwe, J. Velder, S. Blechert, Angew. Chem. 1996, 108, 2542-2544; Angew. Chem. Int. Ed. Engl. 1996, 35, 2376-2378; b) S. D. Burke, M. Müller, C. M. Beaudry, Org. Lett. 1999, 1, 1827-1829; c) H. Oguri, S.-Y. Sasaki, T. Oishi, M. Hirama, Tetrahedron Lett. 1999, 40, 5405-5408; d) M. Lautens, G. Hughes, Angew. Chem. 1999, 111, 160-162; Angew. Chem. Int. Ed. 1999, 38, 129-131; e) G. C. Lloyd-Jones, M. Murray, R. A. Stentiford, P. A. Worthington, Eur. J. Org. Chem. 2000, 975-985; f) D. J. Wallace, C. J. Cowden, D. J. Kennedy, M. S. Ashwood, I. F. Cottrell, U.-H. Dolling, Tetrahedron Lett. 2000, 41, 2027-2029; g) B. Schmidt, M. Westhus, Tetrahedron 2000, 56, 2421-2426; h) D. S. Stoianova, P. R. Hanson, Org. Lett. 2000, 2, 1769-1772; i) Y. Fukuda, H. Sasaki, M. Shindo, K. Shishido, Tetrahedron Lett. 2002, 43, 2047-2049; j) M. Ogasawara, T. Nagano, T. Hayashi, J. Am. Chem. Soc. 2002, 124, 9068-9069.
32. For examples of diastereoselective ring-closing-metathesis reactions, see: a) C. M. Huwe, J. Velder, S. Blechert, Angew. Chem. 1996, 108, 2542-2544; Angew. Chem. Int. Ed. Engl. 1996, 35, 2376-2378; b) S. D. Burke, M. Müller, C. M. Beaudry, Org. Lett. 1999, 1, 1827-1829; c) H. Oguri, S.-Y. Sasaki, T. Oishi, M. Hirama, Tetrahedron Lett. 1999, 40, 5405-5408; d) M. Lautens, G. Hughes, Angew. Chem. 1999, 111, 160-162; Angew. Chem. Int. Ed. 1999, 38, 129-131; e) G. C. Lloyd-Jones, M. Murray, R. A. Stentiford, P. A. Worthington, Eur. J. Org. Chem. 2000, 975-985; f) D. J. Wallace, C. J. Cowden, D. J. Kennedy, M. S. Ashwood, I. F. Cottrell, U.-H. Dolling, Tetrahedron Lett. 2000, 41, 2027-2029; g) B. Schmidt, M. Westhus, Tetrahedron 2000, 56, 2421-2426; h) D. S. Stoianova, P. R. Hanson, Org. Lett. 2000, 2, 1769-1772; i) Y. Fukuda, H. Sasaki, M. Shindo, K. Shishido, Tetrahedron Lett. 2002, 43, 2047-2049; j) M. Ogasawara, T. Nagano, T. Hayashi, J. Am. Chem. Soc. 2002, 124, 9068-9069.
33. For reviews on temporary silicon-tethered strategies, see: a) L. Fensterbank, M. Malacria, S. M. Sieburth, Synthesis 1997, 813-854; b) D. R. Gauthier, Jr., K. S. Zandi, K. J. Shea, Tetrahedron 1998, 54, 2289-2338.
34. For reviews on temporary silicon-tethered strategies, see: a) L. Fensterbank, M. Malacria, S. M. Sieburth, Synthesis 1997, 813-854; b) D. R. Gauthier, Jr., K. S. Zandi, K. J. Shea, Tetrahedron 1998, 54, 2289-2338.
35. S. M. Sieburth, L. Fensterbank, J. Org. Chem. 1992, 57, 5279-5281.
36. a) R. R. Schrock, J. S. Murdzek, G. C. Bazan, J. Robbins, M. DiMare, M. O'Regan, J. Am. Chem. Soc. 1990, 112, 3875-3886;
37. b) P. Schwab, R. H. Grubbs, J. W. Ziller, J. Am. Chem. Soc. 1996, 118, 100-110;
38. c) M. Scholl, S. Ding, C. W. Lee, R. H. Grubbs, Org. Lett. 1999, 1, 953-956.
39. The major stereoisomer was confirmed from nOe experiments in each case (8a-i). Details are available in the Supporting Information.
40. The silyl tether can be readily removed in each case to afford the corresponding diol. For example, treatment of 8 f with 5 % aqueous HF at room temperature furnished the bisallylic 1,4-diol 16 in 99% yield.
41. Although Grubbs' catalyst 10 was not optimal for the larger rings, it also furnished 15 as the major diastereoisomer, which confirmed that the catalyst was not responsible for the reversal in selectivity.
42. The diastereoselectivities in Figure 3, refer to crude product ratios, whereas the selectivities in Table 3 are for the purified silaketals 14a-d and 15a-d.