Tandem Transformations Involving Allylic Silanes. 2. Highly Diastereoselective Substitutions Involving [(Trialkylsilyl)methyl]cyclohexene Derivatives with Aldehydes. Synthetic Studies on the Problem of Lewis Acid-Promoted Protodesilylation and Enolization

Journal of Organic Chemistry

Volumn 62, Issue 16, 1997, Pages 5254-5266

  Organ, Michael G ^a   Winkle, Derick D ^a   Huffmann, John ^b  

^a INDIANA UNIVERSITY   (United States)

^b INDIANA UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0041540779     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970821v     Document Type: Article

References (108)

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2. For recent reviews on tandem chemistry, see: (a) Ho, T.-L. Tandem Organic Reactions; Wiley: New York, 1992. (b) Bunce, R. A. Tetrahedron 1995, 51, 13103-13159. (c) Parsons, P. J.; Penkett, C. S.; Shell, A. J. Chem. Rev. 1995, 95, 195-206. (d) Tietze, L. F. Chem. Rev 1995, 95, 115-136. (e) Denmark, S. E.; Thorarensen, A. Chem. Ron 1996, 96, 137-165.
3. For recent reviews on tandem chemistry, see: (a) Ho, T.-L. Tandem Organic Reactions; Wiley: New York, 1992. (b) Bunce, R. A. Tetrahedron 1995, 51, 13103-13159. (c) Parsons, P. J.; Penkett, C. S.; Shell, A. J. Chem. Rev. 1995, 95, 195-206. (d) Tietze, L. F. Chem. Rev 1995, 95, 115-136. (e) Denmark, S. E.; Thorarensen, A. Chem. Ron 1996, 96, 137-165.
4. For recent reviews on tandem chemistry, see: (a) Ho, T.-L. Tandem Organic Reactions; Wiley: New York, 1992. (b) Bunce, R. A. Tetrahedron 1995, 51, 13103-13159. (c) Parsons, P. J.; Penkett, C. S.; Shell, A. J. Chem. Rev. 1995, 95, 195-206. (d) Tietze, L. F. Chem. Rev 1995, 95, 115-136. (e) Denmark, S. E.; Thorarensen, A. Chem. Ron 1996, 96, 137-165.
5. For recent reviews on tandem chemistry, see: (a) Ho, T.-L. Tandem Organic Reactions; Wiley: New York, 1992. (b) Bunce, R. A. Tetrahedron 1995, 51, 13103-13159. (c) Parsons, P. J.; Penkett, C. S.; Shell, A. J. Chem. Rev. 1995, 95, 195-206. (d) Tietze, L. F. Chem. Rev 1995, 95, 115-136. (e) Denmark, S. E.; Thorarensen, A. Chem. Ron 1996, 96, 137-165.
6. For recent reviews on tandem chemistry, see: (a) Ho, T.-L. Tandem Organic Reactions; Wiley: New York, 1992. (b) Bunce, R. A. Tetrahedron 1995, 51, 13103-13159. (c) Parsons, P. J.; Penkett, C. S.; Shell, A. J. Chem. Rev. 1995, 95, 195-206. (d) Tietze, L. F. Chem. Rev 1995, 95, 115-136. (e) Denmark, S. E.; Thorarensen, A. Chem. Ron 1996, 96, 137-165.
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14. For tandem transition-metal-catalyzed cross-coupling procedures, see: (a) Reiser, O.; Weber, M.; de Meijere, A. Angew. Chem., Int. Ed. Engl. 1989, 59, 74-79. (b) Albrecht, K.; Reiser, O.; Weber, M.; de Meijere, A. Synlett 1992, 521-523. (c) Grigg, R.; Sridharan, V. Tetrahedron Lett. 1992, 33, 7965-7968. (d) Grigg, R.; Kennewell, P.; Teasdale, A.; Sridharan, V. Tetrahedron Lett. 1993, 34, 153-156. (e) Harris, G. D., Jr.; Herr, R. J.; Weinreb, S. M. J. Org. Chem. 1993, 58, 5452-5464. (f) Brown, D.; Grigg, R.; Sridharan, V.; Tambyrajah, V. Tetrahedron Lett. 1995, 36, 8137-8140.
15. For tandem transition-metal-catalyzed cross-coupling procedures, see: (a) Reiser, O.; Weber, M.; de Meijere, A. Angew. Chem., Int. Ed. Engl. 1989, 59, 74-79. (b) Albrecht, K.; Reiser, O.; Weber, M.; de Meijere, A. Synlett 1992, 521-523. (c) Grigg, R.; Sridharan, V. Tetrahedron Lett. 1992, 33, 7965-7968. (d) Grigg, R.; Kennewell, P.; Teasdale, A.; Sridharan, V. Tetrahedron Lett. 1993, 34, 153-156. (e) Harris, G. D., Jr.; Herr, R. J.; Weinreb, S. M. J. Org. Chem. 1993, 58, 5452-5464. (f) Brown, D.; Grigg, R.; Sridharan, V.; Tambyrajah, V. Tetrahedron Lett. 1995, 36, 8137-8140.
16. For tandem transition-metal-catalyzed cross-coupling procedures, see: (a) Reiser, O.; Weber, M.; de Meijere, A. Angew. Chem., Int. Ed. Engl. 1989, 59, 74-79. (b) Albrecht, K.; Reiser, O.; Weber, M.; de Meijere, A. Synlett 1992, 521-523. (c) Grigg, R.; Sridharan, V. Tetrahedron Lett. 1992, 33, 7965-7968. (d) Grigg, R.; Kennewell, P.; Teasdale, A.; Sridharan, V. Tetrahedron Lett. 1993, 34, 153-156. (e) Harris, G. D., Jr.; Herr, R. J.; Weinreb, S. M. J. Org. Chem. 1993, 58, 5452-5464. (f) Brown, D.; Grigg, R.; Sridharan, V.; Tambyrajah, V. Tetrahedron Lett. 1995, 36, 8137-8140.
17. For tandem transition-metal-catalyzed cross-coupling procedures, see: (a) Reiser, O.; Weber, M.; de Meijere, A. Angew. Chem., Int. Ed. Engl. 1989, 59, 74-79. (b) Albrecht, K.; Reiser, O.; Weber, M.; de Meijere, A. Synlett 1992, 521-523. (c) Grigg, R.; Sridharan, V. Tetrahedron Lett. 1992, 33, 7965-7968. (d) Grigg, R.; Kennewell, P.; Teasdale, A.; Sridharan, V. Tetrahedron Lett. 1993, 34, 153-156. (e) Harris, G. D., Jr.; Herr, R. J.; Weinreb, S. M. J. Org. Chem. 1993, 58, 5452-5464. (f) Brown, D.; Grigg, R.; Sridharan, V.; Tambyrajah, V. Tetrahedron Lett. 1995, 36, 8137-8140.
18. For tandem transition-metal-catalyzed cross-coupling procedures, see: (a) Reiser, O.; Weber, M.; de Meijere, A. Angew. Chem., Int. Ed. Engl. 1989, 59, 74-79. (b) Albrecht, K.; Reiser, O.; Weber, M.; de Meijere, A. Synlett 1992, 521-523. (c) Grigg, R.; Sridharan, V. Tetrahedron Lett. 1992, 33, 7965-7968. (d) Grigg, R.; Kennewell, P.; Teasdale, A.; Sridharan, V. Tetrahedron Lett. 1993, 34, 153-156. (e) Harris, G. D., Jr.; Herr, R. J.; Weinreb, S. M. J. Org. Chem. 1993, 58, 5452-5464. (f) Brown, D.; Grigg, R.; Sridharan, V.; Tambyrajah, V. Tetrahedron Lett. 1995, 36, 8137-8140.
19. For tandem transition-metal-catalyzed cross-coupling procedures, see: (a) Reiser, O.; Weber, M.; de Meijere, A. Angew. Chem., Int. Ed. Engl. 1989, 59, 74-79. (b) Albrecht, K.; Reiser, O.; Weber, M.; de Meijere, A. Synlett 1992, 521-523. (c) Grigg, R.; Sridharan, V. Tetrahedron Lett. 1992, 33, 7965-7968. (d) Grigg, R.; Kennewell, P.; Teasdale, A.; Sridharan, V. Tetrahedron Lett. 1993, 34, 153-156. (e) Harris, G. D., Jr.; Herr, R. J.; Weinreb, S. M. J. Org. Chem. 1993, 58, 5452-5464. (f) Brown, D.; Grigg, R.; Sridharan, V.; Tambyrajah, V. Tetrahedron Lett. 1995, 36, 8137-8140.
20. For tandem transition-metal-catalyzed cross-coupling procedures involving carbonylation, see: (a) Crisp, G. T.; Scott, W. J.; Stille, J. K. J. Am. Chem. Soc. 1984, 106, 7500-7506. (b) Chiba, K.; Mori, M.; Ban, Y. Tetrahedron 1985, 41, 387-392. (c) Oppolzer, W.; Bienayme, H.; Genevois-Borella, A. J. Am. Chem. Soc. 1991, 113, 9660-9661. (d) Crisp, G. T.; Meyer, A. G. J. Org. Chem. 1992, 57, 6972-6975. (e) Anderson, P. G.; Aranyos, A. Tetrahedron Lett. 1994, 35, 4441-4444. (f) Grigg, R.; Sridharan, V.; Suganthan, S.; Bridge, A. W. Tetrahedron 1995, 51, 295-306.
21. For tandem transition-metal-catalyzed cross-coupling procedures involving carbonylation, see: (a) Crisp, G. T.; Scott, W. J.; Stille, J. K. J. Am. Chem. Soc. 1984, 106, 7500-7506. (b) Chiba, K.; Mori, M.; Ban, Y. Tetrahedron 1985, 41, 387-392. (c) Oppolzer, W.; Bienayme, H.; Genevois-Borella, A. J. Am. Chem. Soc. 1991, 113, 9660-9661. (d) Crisp, G. T.; Meyer, A. G. J. Org. Chem. 1992, 57, 6972-6975. (e) Anderson, P. G.; Aranyos, A. Tetrahedron Lett. 1994, 35, 4441-4444. (f) Grigg, R.; Sridharan, V.; Suganthan, S.; Bridge, A. W. Tetrahedron 1995, 51, 295-306.
22. For tandem transition-metal-catalyzed cross-coupling procedures involving carbonylation, see: (a) Crisp, G. T.; Scott, W. J.; Stille, J. K. J. Am. Chem. Soc. 1984, 106, 7500-7506. (b) Chiba, K.; Mori, M.; Ban, Y. Tetrahedron 1985, 41, 387-392. (c) Oppolzer, W.; Bienayme, H.; Genevois-Borella, A. J. Am. Chem. Soc. 1991, 113, 9660-9661. (d) Crisp, G. T.; Meyer, A. G. J. Org. Chem. 1992, 57, 6972-6975. (e) Anderson, P. G.; Aranyos, A. Tetrahedron Lett. 1994, 35, 4441-4444. (f) Grigg, R.; Sridharan, V.; Suganthan, S.; Bridge, A. W. Tetrahedron 1995, 51, 295-306.
23. For tandem transition-metal-catalyzed cross-coupling procedures involving carbonylation, see: (a) Crisp, G. T.; Scott, W. J.; Stille, J. K. J. Am. Chem. Soc. 1984, 106, 7500-7506. (b) Chiba, K.; Mori, M.; Ban, Y. Tetrahedron 1985, 41, 387-392. (c) Oppolzer, W.; Bienayme, H.; Genevois-Borella, A. J. Am. Chem. Soc. 1991, 113, 9660-9661. (d) Crisp, G. T.; Meyer, A. G. J. Org. Chem. 1992, 57, 6972-6975. (e) Anderson, P. G.; Aranyos, A. Tetrahedron Lett. 1994, 35, 4441-4444. (f) Grigg, R.; Sridharan, V.; Suganthan, S.; Bridge, A. W. Tetrahedron 1995, 51, 295-306.
24. For tandem transition-metal-catalyzed cross-coupling procedures involving carbonylation, see: (a) Crisp, G. T.; Scott, W. J.; Stille, J. K. J. Am. Chem. Soc. 1984, 106, 7500-7506. (b) Chiba, K.; Mori, M.; Ban, Y. Tetrahedron 1985, 41, 387-392. (c) Oppolzer, W.; Bienayme, H.; Genevois-Borella, A. J. Am. Chem. Soc. 1991, 113, 9660-9661. (d) Crisp, G. T.; Meyer, A. G. J. Org. Chem. 1992, 57, 6972-6975. (e) Anderson, P. G.; Aranyos, A. Tetrahedron Lett. 1994, 35, 4441-4444. (f) Grigg, R.; Sridharan, V.; Suganthan, S.; Bridge, A. W. Tetrahedron 1995, 51, 295-306.
25. For tandem transition-metal-catalyzed cross-coupling procedures involving carbonylation, see: (a) Crisp, G. T.; Scott, W. J.; Stille, J. K. J. Am. Chem. Soc. 1984, 106, 7500-7506. (b) Chiba, K.; Mori, M.; Ban, Y. Tetrahedron 1985, 41, 387-392. (c) Oppolzer, W.; Bienayme, H.; Genevois-Borella, A. J. Am. Chem. Soc. 1991, 113, 9660-9661. (d) Crisp, G. T.; Meyer, A. G. J. Org. Chem. 1992, 57, 6972-6975. (e) Anderson, P. G.; Aranyos, A. Tetrahedron Lett. 1994, 35, 4441-4444. (f) Grigg, R.; Sridharan, V.; Suganthan, S.; Bridge, A. W. Tetrahedron 1995, 51, 295-306.
26. For tandem transition-metal-catalyzed cycloisomerization procedures, see: (a) Oppolzer, W.; DeVita, R. J. J. Org. Chem. 1991, 56, 6256-6257. (b) Meyer, F. E.; Brandenburg, J.; Parsons, P. J.; de Meijere, A. J. Chem. Soc., Chem. Commun. 1992, 390-392. (c) Trost, B. M.; Shi, Y. J. Am. Chem. Soc. 1992, 114, 791-792. (d) Trost, B. M.; Dumas, J. J. Am. Chem. Soc. 1992, 114, 1924-1925. (e) Trost, B. M.; Shi, Y. J. Am. Chem. Soc. 1992, 114, 791-792. (f) Trost, B. M.; Shi, Y. J. Am. Chem. Soc. 1993, 115, 12491-12509.
27. For tandem transition-metal-catalyzed cycloisomerization procedures, see: (a) Oppolzer, W.; DeVita, R. J. J. Org. Chem. 1991, 56, 6256-6257. (b) Meyer, F. E.; Brandenburg, J.; Parsons, P. J.; de Meijere, A. J. Chem. Soc., Chem. Commun. 1992, 390-392. (c) Trost, B. M.; Shi, Y. J. Am. Chem. Soc. 1992, 114, 791-792. (d) Trost, B. M.; Dumas, J. J. Am. Chem. Soc. 1992, 114, 1924-1925. (e) Trost, B. M.; Shi, Y. J. Am. Chem. Soc. 1992, 114, 791-792. (f) Trost, B. M.; Shi, Y. J. Am. Chem. Soc. 1993, 115, 12491-12509.
28. For tandem transition-metal-catalyzed cycloisomerization procedures, see: (a) Oppolzer, W.; DeVita, R. J. J. Org. Chem. 1991, 56, 6256-6257. (b) Meyer, F. E.; Brandenburg, J.; Parsons, P. J.; de Meijere, A. J. Chem. Soc., Chem. Commun. 1992, 390-392. (c) Trost, B. M.; Shi, Y. J. Am. Chem. Soc. 1992, 114, 791-792. (d) Trost, B. M.; Dumas, J. J. Am. Chem. Soc. 1992, 114, 1924-1925. (e) Trost, B. M.; Shi, Y. J. Am. Chem. Soc. 1992, 114, 791-792. (f) Trost, B. M.; Shi, Y. J. Am. Chem. Soc. 1993, 115, 12491-12509.
29. For tandem transition-metal-catalyzed cycloisomerization procedures, see: (a) Oppolzer, W.; DeVita, R. J. J. Org. Chem. 1991, 56, 6256-6257. (b) Meyer, F. E.; Brandenburg, J.; Parsons, P. J.; de Meijere, A. J. Chem. Soc., Chem. Commun. 1992, 390-392. (c) Trost, B. M.; Shi, Y. J. Am. Chem. Soc. 1992, 114, 791-792. (d) Trost, B. M.; Dumas, J. J. Am. Chem. Soc. 1992, 114, 1924-1925. (e) Trost, B. M.; Shi, Y. J. Am. Chem. Soc. 1992, 114, 791-792. (f) Trost, B. M.; Shi, Y. J. Am. Chem. Soc. 1993, 115, 12491-12509.
30. For tandem transition-metal-catalyzed cycloisomerization procedures, see: (a) Oppolzer, W.; DeVita, R. J. J. Org. Chem. 1991, 56, 6256-6257. (b) Meyer, F. E.; Brandenburg, J.; Parsons, P. J.; de Meijere, A. J. Chem. Soc., Chem. Commun. 1992, 390-392. (c) Trost, B. M.; Shi, Y. J. Am. Chem. Soc. 1992, 114, 791-792. (d) Trost, B. M.; Dumas, J. J. Am. Chem. Soc. 1992, 114, 1924-1925. (e) Trost, B. M.; Shi, Y. J. Am. Chem. Soc. 1992, 114, 791-792. (f) Trost, B. M.; Shi, Y. J. Am. Chem. Soc. 1993, 115, 12491-12509.
31. For tandem transition-metal-catalyzed cycloisomerization procedures, see: (a) Oppolzer, W.; DeVita, R. J. J. Org. Chem. 1991, 56, 6256-6257. (b) Meyer, F. E.; Brandenburg, J.; Parsons, P. J.; de Meijere, A. J. Chem. Soc., Chem. Commun. 1992, 390-392. (c) Trost, B. M.; Shi, Y. J. Am. Chem. Soc. 1992, 114, 791-792. (d) Trost, B. M.; Dumas, J. J. Am. Chem. Soc. 1992, 114, 1924-1925. (e) Trost, B. M.; Shi, Y. J. Am. Chem. Soc. 1992, 114, 791-792. (f) Trost, B. M.; Shi, Y. J. Am. Chem. Soc. 1993, 115, 12491-12509.
32. For examples of tandem reactions where each step in the sequence is of different mechanism, see: (a) Tietze, L.-F.; von Kiedrowski, G.; Berger, B. Angew. Chem., Int. Ed. Engl. 1982, 21, 221-224. (b) Tietze, L. F.; von Kiedrowski, G.; Berger, B. Synthesis 1982, 683-687. (c) Xu, Y.-C.; Cantin, M.; Deslongchamps, P. Can. J. Chem. 1990, 68, 2137-2143. (d) Davies, H. W.; Saikali, E.; Young, W. B. J. Org. Chem. 1991, 56, 5696-5700. Also see ref 2.
33. For examples of tandem reactions where each step in the sequence is of different mechanism, see: (a) Tietze, L.-F.; von Kiedrowski, G.; Berger, B. Angew. Chem., Int. Ed. Engl. 1982, 21, 221-224. (b) Tietze, L. F.; von Kiedrowski, G.; Berger, B. Synthesis 1982, 683-687. (c) Xu, Y.-C.; Cantin, M.; Deslongchamps, P. Can. J. Chem. 1990, 68, 2137-2143. (d) Davies, H. W.; Saikali, E.; Young, W. B. J. Org. Chem. 1991, 56, 5696-5700. Also see ref 2.
34. For examples of tandem reactions where each step in the sequence is of different mechanism, see: (a) Tietze, L.-F.; von Kiedrowski, G.; Berger, B. Angew. Chem., Int. Ed. Engl. 1982, 21, 221-224. (b) Tietze, L. F.; von Kiedrowski, G.; Berger, B. Synthesis 1982, 683-687. (c) Xu, Y.-C.; Cantin, M.; Deslongchamps, P. Can. J. Chem. 1990, 68, 2137-2143. (d) Davies, H. W.; Saikali, E.; Young, W. B. J. Org. Chem. 1991, 56, 5696-5700. Also see ref 2.
35. For examples of tandem reactions where each step in the sequence is of different mechanism, see: (a) Tietze, L.-F.; von Kiedrowski, G.; Berger, B. Angew. Chem., Int. Ed. Engl. 1982, 21, 221-224. (b) Tietze, L. F.; von Kiedrowski, G.; Berger, B. Synthesis 1982, 683-687. (c) Xu, Y.-C.; Cantin, M.; Deslongchamps, P. Can. J. Chem. 1990, 68, 2137-2143. (d) Davies, H. W.; Saikali, E.; Young, W. B. J. Org. Chem. 1991, 56, 5696-5700. Also see ref 2.
36. For general reviews concerning the use of allylsilanes in organic synthesis, see: (a) Fleming, I. Chem. Soc. Rev. 1981, 10, 83-111. (b) Parnes, Z. N.; Bolestova, G. I. Synthesis 1984, 991-1008. (c) Blumenkopf, T. A.; Overman, L. E. Chem. Rev. 1986, 86, 857-873. (d) Schinzer, D. Synthesis 1988, 263-273. (e) Fleming, I.; Dunogues, J.; Smithers, R. Org. React. 1989, 31, 57-575. (f) Chan, T. H.; Wang, D.; Pellon, P.; Lamothe, S.; Wie, Z. Y.; Li, L. H.; Chen, L. M. Enantioselective synthesis using silicon compounds. Frontiers of Organosilicon Chemistry; The Royal Society of Chemistry: London, 1991; p 344-355. (g) Colvin, E. W.; Loreto, M. A.; Montieth, M.; Tommasini, I. Frontiers of Organosilicon Chemistry; The Royal Society of Chemistry, London, 1991; p 356. (h) Langkopf, E.; Schinzer, D. Chem. Rev. 1995, 95, 1375-1408.
37. For general reviews concerning the use of allylsilanes in organic synthesis, see: (a) Fleming, I. Chem. Soc. Rev. 1981, 10, 83-111. (b) Parnes, Z. N.; Bolestova, G. I. Synthesis 1984, 991-1008. (c) Blumenkopf, T. A.; Overman, L. E. Chem. Rev. 1986, 86, 857-873. (d) Schinzer, D. Synthesis 1988, 263-273. (e) Fleming, I.; Dunogues, J.; Smithers, R. Org. React. 1989, 31, 57-575. (f) Chan, T. H.; Wang, D.; Pellon, P.; Lamothe, S.; Wie, Z. Y.; Li, L. H.; Chen, L. M. Enantioselective synthesis using silicon compounds. Frontiers of Organosilicon Chemistry; The Royal Society of Chemistry: London, 1991; p 344-355. (g) Colvin, E. W.; Loreto, M. A.; Montieth, M.; Tommasini, I. Frontiers of Organosilicon Chemistry; The Royal Society of Chemistry, London, 1991; p 356. (h) Langkopf, E.; Schinzer, D. Chem. Rev. 1995, 95, 1375-1408.
38. For general reviews concerning the use of allylsilanes in organic synthesis, see: (a) Fleming, I. Chem. Soc. Rev. 1981, 10, 83-111. (b) Parnes, Z. N.; Bolestova, G. I. Synthesis 1984, 991-1008. (c) Blumenkopf, T. A.; Overman, L. E. Chem. Rev. 1986, 86, 857-873. (d) Schinzer, D. Synthesis 1988, 263-273. (e) Fleming, I.; Dunogues, J.; Smithers, R. Org. React. 1989, 31, 57-575. (f) Chan, T. H.; Wang, D.; Pellon, P.; Lamothe, S.; Wie, Z. Y.; Li, L. H.; Chen, L. M. Enantioselective synthesis using silicon compounds. Frontiers of Organosilicon Chemistry; The Royal Society of Chemistry: London, 1991; p 344-355. (g) Colvin, E. W.; Loreto, M. A.; Montieth, M.; Tommasini, I. Frontiers of Organosilicon Chemistry; The Royal Society of Chemistry, London, 1991; p 356. (h) Langkopf, E.; Schinzer, D. Chem. Rev. 1995, 95, 1375-1408.
39. For general reviews concerning the use of allylsilanes in organic synthesis, see: (a) Fleming, I. Chem. Soc. Rev. 1981, 10, 83-111. (b) Parnes, Z. N.; Bolestova, G. I. Synthesis 1984, 991-1008. (c) Blumenkopf, T. A.; Overman, L. E. Chem. Rev. 1986, 86, 857-873. (d) Schinzer, D. Synthesis 1988, 263-273. (e) Fleming, I.; Dunogues, J.; Smithers, R. Org. React. 1989, 31, 57-575. (f) Chan, T. H.; Wang, D.; Pellon, P.; Lamothe, S.; Wie, Z. Y.; Li, L. H.; Chen, L. M. Enantioselective synthesis using silicon compounds. Frontiers of Organosilicon Chemistry; The Royal Society of Chemistry: London, 1991; p 344-355. (g) Colvin, E. W.; Loreto, M. A.; Montieth, M.; Tommasini, I. Frontiers of Organosilicon Chemistry; The Royal Society of Chemistry, London, 1991; p 356. (h) Langkopf, E.; Schinzer, D. Chem. Rev. 1995, 95, 1375-1408.
40. For general reviews concerning the use of allylsilanes in organic synthesis, see: (a) Fleming, I. Chem. Soc. Rev. 1981, 10, 83-111. (b) Parnes, Z. N.; Bolestova, G. I. Synthesis 1984, 991-1008. (c) Blumenkopf, T. A.; Overman, L. E. Chem. Rev. 1986, 86, 857-873. (d) Schinzer, D. Synthesis 1988, 263-273. (e) Fleming, I.; Dunogues, J.; Smithers, R. Org. React. 1989, 31, 57-575. (f) Chan, T. H.; Wang, D.; Pellon, P.; Lamothe, S.; Wie, Z. Y.; Li, L. H.; Chen, L. M. Enantioselective synthesis using silicon compounds. Frontiers of Organosilicon Chemistry; The Royal Society of Chemistry: London, 1991; p 344-355. (g) Colvin, E. W.; Loreto, M. A.; Montieth, M.; Tommasini, I. Frontiers of Organosilicon Chemistry; The Royal Society of Chemistry, London, 1991; p 356. (h) Langkopf, E.; Schinzer, D. Chem. Rev. 1995, 95, 1375-1408.
41. For general reviews concerning the use of allylsilanes in organic synthesis, see: (a) Fleming, I. Chem. Soc. Rev. 1981, 10, 83-111. (b) Parnes, Z. N.; Bolestova, G. I. Synthesis 1984, 991-1008. (c) Blumenkopf, T. A.; Overman, L. E. Chem. Rev. 1986, 86, 857-873. (d) Schinzer, D. Synthesis 1988, 263-273. (e) Fleming, I.; Dunogues, J.; Smithers, R. Org. React. 1989, 31, 57-575. (f) Chan, T. H.; Wang, D.; Pellon, P.; Lamothe, S.; Wie, Z. Y.; Li, L. H.; Chen, L. M. Enantioselective synthesis using silicon compounds. Frontiers of Organosilicon Chemistry; The Royal Society of Chemistry: London, 1991; p 344-355. (g) Colvin, E. W.; Loreto, M. A.; Montieth, M.; Tommasini, I. Frontiers of Organosilicon Chemistry; The Royal Society of Chemistry, London, 1991; p 356. (h) Langkopf, E.; Schinzer, D. Chem. Rev. 1995, 95, 1375-1408.
42. For general reviews concerning the use of allylsilanes in organic synthesis, see: (a) Fleming, I. Chem. Soc. Rev. 1981, 10, 83-111. (b) Parnes, Z. N.; Bolestova, G. I. Synthesis 1984, 991-1008. (c) Blumenkopf, T. A.; Overman, L. E. Chem. Rev. 1986, 86, 857-873. (d) Schinzer, D. Synthesis 1988, 263-273. (e) Fleming, I.; Dunogues, J.; Smithers, R. Org. React. 1989, 31, 57-575. (f) Chan, T. H.; Wang, D.; Pellon, P.; Lamothe, S.; Wie, Z. Y.; Li, L. H.; Chen, L. M. Enantioselective synthesis using silicon compounds. Frontiers of Organosilicon Chemistry; The Royal Society of Chemistry: London, 1991; p 344-355. (g) Colvin, E. W.; Loreto, M. A.; Montieth, M.; Tommasini, I. Frontiers of Organosilicon Chemistry; The Royal Society of Chemistry, London, 1991; p 356. (h) Langkopf, E.; Schinzer, D. Chem. Rev. 1995, 95, 1375-1408.
43. For general reviews concerning the use of allylsilanes in organic synthesis, see: (a) Fleming, I. Chem. Soc. Rev. 1981, 10, 83-111. (b) Parnes, Z. N.; Bolestova, G. I. Synthesis 1984, 991-1008. (c) Blumenkopf, T. A.; Overman, L. E. Chem. Rev. 1986, 86, 857-873. (d) Schinzer, D. Synthesis 1988, 263-273. (e) Fleming, I.; Dunogues, J.; Smithers, R. Org. React. 1989, 31, 57-575. (f) Chan, T. H.; Wang, D.; Pellon, P.; Lamothe, S.; Wie, Z. Y.; Li, L. H.; Chen, L. M. Enantioselective synthesis using silicon compounds. Frontiers of Organosilicon Chemistry; The Royal Society of Chemistry: London, 1991; p 344-355. (g) Colvin, E. W.; Loreto, M. A.; Montieth, M.; Tommasini, I. Frontiers of Organosilicon Chemistry; The Royal Society of Chemistry, London, 1991; p 356. (h) Langkopf, E.; Schinzer, D. Chem. Rev. 1995, 95, 1375-1408.
44. For discussion related to the use of silyl-stabilized radicals in synthesis, see: (a) Auner, N.; Walsh, R.; Westrup, J. J. Chem. Soc., Chem. Commun. 1986, 207-208. (b) Wilt, J. W.; Lusztyk, J.; Peeran, M.; Ingold, K. U. J. Am. Chem. Soc. 1988, 110, 281-287.
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48. (b) Eaborn, C. J. Chem. Soc., Chem. Commun. 1972, 1255. (c) Fleming, I. Frontier Orbitals and Organic Chemical Reactions; Wiley: London, 1976; p 81. (d) Wierschke, S. G.; Chandrasekhar, J.; Jorgensen, W. L. J. Am. Chem. Soc. 1985, 107, 1496-1500. (e) Lambert, J. B. Tetrahedron 1990, 46, 2677-2689.
49. (b) Eaborn, C. J. Chem. Soc., Chem. Commun. 1972, 1255. (c) Fleming, I. Frontier Orbitals and Organic Chemical Reactions; Wiley: London, 1976; p 81. (d) Wierschke, S. G.; Chandrasekhar, J.; Jorgensen, W. L. J. Am. Chem. Soc. 1985, 107, 1496-1500. (e) Lambert, J. B. Tetrahedron 1990, 46, 2677-2689.
50. (b) Eaborn, C. J. Chem. Soc., Chem. Commun. 1972, 1255. (c) Fleming, I. Frontier Orbitals and Organic Chemical Reactions; Wiley: London, 1976; p 81. (d) Wierschke, S. G.; Chandrasekhar, J.; Jorgensen, W. L. J. Am. Chem. Soc. 1985, 107, 1496-1500. (e) Lambert, J. B. Tetrahedron 1990, 46, 2677-2689.
51. For uses of allylsilanes in anion-mediated transformations, see: (a) Yamamoto, Y.; Saito, Y.; Naruyam, K. J. Org. Chem. 1980, 45, 195-196. (b) Tsai, D. J. S.; Matteson, D. S. Tetrahedron Lett. 1981, 22, 2751-2752. (c) Tamao, K.; Nakajo, E.; Ito, Y. Tetrahedron 1988, 44, 3997-4007. (d) Chan, T. H.; Pellon, P. J. Am. Chem. Soc. 1989, 111, 8737-8738. (e) Chan, T. H.; Horvath, R. F. J. Org. Chem. 1989, 54, 317-327. (f) Chan, T. H.; Wang, D. Chem. Rev. 1995, 95, 1279-1292.
52. For uses of allylsilanes in anion-mediated transformations, see: (a) Yamamoto, Y.; Saito, Y.; Naruyam, K. J. Org. Chem. 1980, 45, 195-196. (b) Tsai, D. J. S.; Matteson, D. S. Tetrahedron Lett. 1981, 22, 2751-2752. (c) Tamao, K.; Nakajo, E.; Ito, Y. Tetrahedron 1988, 44, 3997-4007. (d) Chan, T. H.; Pellon, P. J. Am. Chem. Soc. 1989, 111, 8737-8738. (e) Chan, T. H.; Horvath, R. F. J. Org. Chem. 1989, 54, 317-327. (f) Chan, T. H.; Wang, D. Chem. Rev. 1995, 95, 1279-1292.
53. For uses of allylsilanes in anion-mediated transformations, see: (a) Yamamoto, Y.; Saito, Y.; Naruyam, K. J. Org. Chem. 1980, 45, 195-196. (b) Tsai, D. J. S.; Matteson, D. S. Tetrahedron Lett. 1981, 22, 2751-2752. (c) Tamao, K.; Nakajo, E.; Ito, Y. Tetrahedron 1988, 44, 3997-4007. (d) Chan, T. H.; Pellon, P. J. Am. Chem. Soc. 1989, 111, 8737-8738. (e) Chan, T. H.; Horvath, R. F. J. Org. Chem. 1989, 54, 317-327. (f) Chan, T. H.; Wang, D. Chem. Rev. 1995, 95, 1279-1292.
54. For uses of allylsilanes in anion-mediated transformations, see: (a) Yamamoto, Y.; Saito, Y.; Naruyam, K. J. Org. Chem. 1980, 45, 195-196. (b) Tsai, D. J. S.; Matteson, D. S. Tetrahedron Lett. 1981, 22, 2751-2752. (c) Tamao, K.; Nakajo, E.; Ito, Y. Tetrahedron 1988, 44, 3997-4007. (d) Chan, T. H.; Pellon, P. J. Am. Chem. Soc. 1989, 111, 8737-8738. (e) Chan, T. H.; Horvath, R. F. J. Org. Chem. 1989, 54, 317-327. (f) Chan, T. H.; Wang, D. Chem. Rev. 1995, 95, 1279-1292.
55. For uses of allylsilanes in anion-mediated transformations, see: (a) Yamamoto, Y.; Saito, Y.; Naruyam, K. J. Org. Chem. 1980, 45, 195-196. (b) Tsai, D. J. S.; Matteson, D. S. Tetrahedron Lett. 1981, 22, 2751-2752. (c) Tamao, K.; Nakajo, E.; Ito, Y. Tetrahedron 1988, 44, 3997-4007. (d) Chan, T. H.; Pellon, P. J. Am. Chem. Soc. 1989, 111, 8737-8738. (e) Chan, T. H.; Horvath, R. F. J. Org. Chem. 1989, 54, 317-327. (f) Chan, T. H.; Wang, D. Chem. Rev. 1995, 95, 1279-1292.
56. For uses of allylsilanes in anion-mediated transformations, see: (a) Yamamoto, Y.; Saito, Y.; Naruyam, K. J. Org. Chem. 1980, 45, 195-196. (b) Tsai, D. J. S.; Matteson, D. S. Tetrahedron Lett. 1981, 22, 2751-2752. (c) Tamao, K.; Nakajo, E.; Ito, Y. Tetrahedron 1988, 44, 3997-4007. (d) Chan, T. H.; Pellon, P. J. Am. Chem. Soc. 1989, 111, 8737-8738. (e) Chan, T. H.; Horvath, R. F. J. Org. Chem. 1989, 54, 317-327. (f) Chan, T. H.; Wang, D. Chem. Rev. 1995, 95, 1279-1292.
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81. For discussion concerning synclinal and antiperiplanar transition states in allylsilane substitution reactions, see: (a) Hayashi, H.; Ito, H.; Kumada, M. Tetrahedron Lett. 1982, 23, 4605-4606. (b) Hayashi, H.; Konishi, M.; Kumada, M. J. Org. Chem. 1983, 48, 281-282. (c) Denmark, S. E.; Weber, E. J. Helv. Chim. Acta 1983, 66, 1655-1660. (d) Denmark, S. E.; Almstead, N. G. J. Org. Chem. 1994, 59, 5130-5132. (e) Denmark, S. E.; Hosoi, S. J. Org. Chem. 1994, 59, 5133-5135.
82. For discussion concerning synclinal and antiperiplanar transition states in allylsilane substitution reactions, see: (a) Hayashi, H.; Ito, H.; Kumada, M. Tetrahedron Lett. 1982, 23, 4605-4606. (b) Hayashi, H.; Konishi, M.; Kumada, M. J. Org. Chem. 1983, 48, 281-282. (c) Denmark, S. E.; Weber, E. J. Helv. Chim. Acta 1983, 66, 1655-1660. (d) Denmark, S. E.; Almstead, N. G. J. Org. Chem. 1994, 59, 5130-5132. (e) Denmark, S. E.; Hosoi, S. J. Org. Chem. 1994, 59, 5133-5135.
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88. A similar rationale for analogous substitutions involving allylsilanes and acid chlorides has been proposed by other groups; see: (a) Polla, M.; Frejd, T. Acta Chem. Scand. 1993, 47, 716-720. (b) Also see ref 20.
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