New computational and experimental evidence for the mechanism of the Sakurai reaction

Journal of the American Chemical Society

Volumn 119, Issue 50, 1997, Pages 12131-12135

  Bottoni, Andrea ^a   Costa, Anna Luisa ^a   Di Tommaso, Donata ^a   Rossi, Ivan ^a   Tagliavini, Emilio ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ALLYLTRIMETHYLSILANE; FLUOROTRIMETHYLSILANE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; CONFORMATIONAL TRANSITION; CYCLIZATION; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; THERMODYNAMICS;

EID: 0031576689     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9723693     Document Type: Article

References (51)

1. For reviews on the aldehyde allylation see: (a) Fleming, I. Org. React. 1989, 37, 57. (b) Fleming, I. In Comprehensive Organic Synthesis; Heathcock, C. H., Ed.; Pergamon Press: Oxford, 1991; Vol. 2, p 563. (c) Sakurai H. Pure Appl. Chem. 1992, 54, 1. (d) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207. (e) Nishigaichi, Y.; Takuwa, A.; Naruta, Y.; Maruyama, K. Tetrahedron 1993, 49, 7395. (f) Masse, C. E.; Panek, J. S. Chem. Rev. 1995, 95, 1293.
2. For reviews on the aldehyde allylation see: (a) Fleming, I. Org. React. 1989, 37, 57. (b) Fleming, I. In Comprehensive Organic Synthesis; Heathcock, C. H., Ed.; Pergamon Press: Oxford, 1991; Vol. 2, p 563. (c) Sakurai H. Pure Appl. Chem. 1992, 54, 1. (d) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207. (e) Nishigaichi, Y.; Takuwa, A.; Naruta, Y.; Maruyama, K. Tetrahedron 1993, 49, 7395. (f) Masse, C. E.; Panek, J. S. Chem. Rev. 1995, 95, 1293.
3. For reviews on the aldehyde allylation see: (a) Fleming, I. Org. React. 1989, 37, 57. (b) Fleming, I. In Comprehensive Organic Synthesis; Heathcock, C. H., Ed.; Pergamon Press: Oxford, 1991; Vol. 2, p 563. (c) Sakurai H. Pure Appl. Chem. 1992, 54, 1. (d) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207. (e) Nishigaichi, Y.; Takuwa, A.; Naruta, Y.; Maruyama, K. Tetrahedron 1993, 49, 7395. (f) Masse, C. E.; Panek, J. S. Chem. Rev. 1995, 95, 1293.
4. For reviews on the aldehyde allylation see: (a) Fleming, I. Org. React. 1989, 37, 57. (b) Fleming, I. In Comprehensive Organic Synthesis; Heathcock, C. H., Ed.; Pergamon Press: Oxford, 1991; Vol. 2, p 563. (c) Sakurai H. Pure Appl. Chem. 1992, 54, 1. (d) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207. (e) Nishigaichi, Y.; Takuwa, A.; Naruta, Y.; Maruyama, K. Tetrahedron 1993, 49, 7395. (f) Masse, C. E.; Panek, J. S. Chem. Rev. 1995, 95, 1293.
5. For reviews on the aldehyde allylation see: (a) Fleming, I. Org. React. 1989, 37, 57. (b) Fleming, I. In Comprehensive Organic Synthesis; Heathcock, C. H., Ed.; Pergamon Press: Oxford, 1991; Vol. 2, p 563. (c) Sakurai H. Pure Appl. Chem. 1992, 54, 1. (d) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207. (e) Nishigaichi, Y.; Takuwa, A.; Naruta, Y.; Maruyama, K. Tetrahedron 1993, 49, 7395. (f) Masse, C. E.; Panek, J. S. Chem. Rev. 1995, 95, 1293.
6. For reviews on the aldehyde allylation see: (a) Fleming, I. Org. React. 1989, 37, 57. (b) Fleming, I. In Comprehensive Organic Synthesis; Heathcock, C. H., Ed.; Pergamon Press: Oxford, 1991; Vol. 2, p 563. (c) Sakurai H. Pure Appl. Chem. 1992, 54, 1. (d) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207. (e) Nishigaichi, Y.; Takuwa, A.; Naruta, Y.; Maruyama, K. Tetrahedron 1993, 49, 7395. (f) Masse, C. E.; Panek, J. S. Chem. Rev. 1995, 95, 1293.
7. Hosomi, A.; Sakurai, H. Tetrahedron Lett. 1976, 16, 1295.
8. Hayashi, T.; Kabeta, K.; Hamachi, I.; Kumada, M. Tetrahedron Lett. 1983, 24, 2865.
9. Yamamoto, Y.; Maruyama, K.; Naruta, Y.; Yatagai, H. J. Am. Chem. Soc. 1980, 102, 7101.
10. Cyclic transition states have been proposed for the reactions of allylsilacyclobutanes (Matsumoto, K.; Oshima, K.; Utimoto, K. J. Org. Chem. 1994, 59, 7152) and allyltrifluorosilanes (Kobayashi, S.; Nishio, K. J. Org. Chem. 1994, 59, 6620). These transition structures have recently been determined with theoretical methods: Fujimoto, H.; Omoto, K.; Sawada, Y. J. Am. Chem. Soc. 1996, 118, 1750-1755. Also the thermal or pressurized reaction of allylstannanes with aldehydes has been proposed to proceed through cyclic transition states: Yamamoto, Y.; Maruyama, K.; Matsumoto, K. J. Chem. Soc., Chem. Commun. 1983, 489. A theoretical investigation of the allylation with allyl tetrafluorosilicates has shown that reaction involves a cyclyc transition structure: Kira, M.; Sato, K.; Sakurai, H.; Hada, M.; Izawa, M.; Ushio, J. Chem. Lett. 1991, 387.
11. Cyclic transition states have been proposed for the reactions of allylsilacyclobutanes (Matsumoto, K.; Oshima, K.; Utimoto, K. J. Org. Chem. 1994, 59, 7152) and allyltrifluorosilanes (Kobayashi, S.; Nishio, K. J. Org. Chem. 1994, 59, 6620). These transition structures have recently been determined with theoretical methods: Fujimoto, H.; Omoto, K.; Sawada, Y. J. Am. Chem. Soc. 1996, 118, 1750-1755. Also the thermal or pressurized reaction of allylstannanes with aldehydes has been proposed to proceed through cyclic transition states: Yamamoto, Y.; Maruyama, K.; Matsumoto, K. J. Chem. Soc., Chem. Commun. 1983, 489. A theoretical investigation of the allylation with allyl tetrafluorosilicates has shown that reaction involves a cyclyc transition structure: Kira, M.; Sato, K.; Sakurai, H.; Hada, M.; Izawa, M.; Ushio, J. Chem. Lett. 1991, 387.
12. Cyclic transition states have been proposed for the reactions of allylsilacyclobutanes (Matsumoto, K.; Oshima, K.; Utimoto, K. J. Org. Chem. 1994, 59, 7152) and allyltrifluorosilanes (Kobayashi, S.; Nishio, K. J. Org. Chem. 1994, 59, 6620). These transition structures have recently been determined with theoretical methods: Fujimoto, H.; Omoto, K.; Sawada, Y. J. Am. Chem. Soc. 1996, 118, 1750-1755. Also the thermal or pressurized reaction of allylstannanes with aldehydes has been proposed to proceed through cyclic transition states: Yamamoto, Y.; Maruyama, K.; Matsumoto, K. J. Chem. Soc., Chem. Commun. 1983, 489. A theoretical investigation of the allylation with allyl tetrafluorosilicates has shown that reaction involves a cyclyc transition structure: Kira, M.; Sato, K.; Sakurai, H.; Hada, M.; Izawa, M.; Ushio, J. Chem. Lett. 1991, 387.
13. Cyclic transition states have been proposed for the reactions of allylsilacyclobutanes (Matsumoto, K.; Oshima, K.; Utimoto, K. J. Org. Chem. 1994, 59, 7152) and allyltrifluorosilanes (Kobayashi, S.; Nishio, K. J. Org. Chem. 1994, 59, 6620). These transition structures have recently been determined with theoretical methods: Fujimoto, H.; Omoto, K.; Sawada, Y. J. Am. Chem. Soc. 1996, 118, 1750-1755. Also the thermal or pressurized reaction of allylstannanes with aldehydes has been proposed to proceed through cyclic transition states: Yamamoto, Y.; Maruyama, K.; Matsumoto, K. J. Chem. Soc., Chem. Commun. 1983, 489. A theoretical investigation of the allylation with allyl tetrafluorosilicates has shown that reaction involves a cyclyc transition structure: Kira, M.; Sato, K.; Sakurai, H.; Hada, M.; Izawa, M.; Ushio, J. Chem. Lett. 1991, 387.
14. Cyclic transition states have been proposed for the reactions of allylsilacyclobutanes (Matsumoto, K.; Oshima, K.; Utimoto, K. J. Org. Chem. 1994, 59, 7152) and allyltrifluorosilanes (Kobayashi, S.; Nishio, K. J. Org. Chem. 1994, 59, 6620). These transition structures have recently been determined with theoretical methods: Fujimoto, H.; Omoto, K.; Sawada, Y. J. Am. Chem. Soc. 1996, 118, 1750-1755. Also the thermal or pressurized reaction of allylstannanes with aldehydes has been proposed to proceed through cyclic transition states: Yamamoto, Y.; Maruyama, K.; Matsumoto, K. J. Chem. Soc., Chem. Commun. 1983, 489. A theoretical investigation of the allylation with allyl tetrafluorosilicates has shown that reaction involves a cyclyc transition structure: Kira, M.; Sato, K.; Sakurai, H.; Hada, M.; Izawa, M.; Ushio, J. Chem. Lett. 1991, 387.
15. (a) Hayashi, T.; Konishi, M.; Ito, H.; Kumada, M. J. Am. Chem. Soc. 1982, 104, 4962.
16. (b) Hayashi, T.; Konishi, M.; Kumada, M. J. Am. Chem. Soc. 1982, 104, 4963.
17. (c) Wetter, H.; Scherer, P.; Schweizer, W. B. Helv. Chim. Acta 1979, 62, 1985.
18. Denmark, S. E.; Almstead, N. G. J. Org. Chem. 1994, 59, 5130.
19. Yamamoto, Y.; Yatagai, H.; Ishihara, Y.; Maeda, N.; Maruyama, K. Tetrahedron 1984, 40, 2239-2246.
20. Allylsilanes: (a) Denmark, S. E.; Weber, E. J. Helv. Chim. Acta 1983, 66, 1655. (b) Denmark, S. E.; Weber, E. J.; Wilson, T. M.; Tetrahedron 1989, 45, 1053. (c) Mikami, K.; Maeda, T.; Kishi, N.; Nakai, T. Tetrahedron Lett. 1984, 25, 5151. Allylstannanes: (d) Denmark, S. E.; Hosoi, S. J. Org. Chem. 1994, 59, 5133. (e) Keck, G. E.; Dougherty, S. M.; Savin, K. A. J. Am. Chem. Soc. 1995, 117, 6210-6223. (f) Gevorgyan, V.; Kadota, I.; Yamamoto, Y. Tetrahedron Lett. 1993, 34, 1313. See also: Fleming, I Chemtracts 1991, 4, 21.
21. Allylsilanes: (a) Denmark, S. E.; Weber, E. J. Helv. Chim. Acta 1983, 66, 1655. (b) Denmark, S. E.; Weber, E. J.; Wilson, T. M.; Tetrahedron 1989, 45, 1053. (c) Mikami, K.; Maeda, T.; Kishi, N.; Nakai, T. Tetrahedron Lett. 1984, 25, 5151. Allylstannanes: (d) Denmark, S. E.; Hosoi, S. J. Org. Chem. 1994, 59, 5133. (e) Keck, G. E.; Dougherty, S. M.; Savin, K. A. J. Am. Chem. Soc. 1995, 117, 6210-6223. (f) Gevorgyan, V.; Kadota, I.; Yamamoto, Y. Tetrahedron Lett. 1993, 34, 1313. See also: Fleming, I Chemtracts 1991, 4, 21.
22. Allylsilanes: (a) Denmark, S. E.; Weber, E. J. Helv. Chim. Acta 1983, 66, 1655. (b) Denmark, S. E.; Weber, E. J.; Wilson, T. M.; Tetrahedron 1989, 45, 1053. (c) Mikami, K.; Maeda, T.; Kishi, N.; Nakai, T. Tetrahedron Lett. 1984, 25, 5151. Allylstannanes: (d) Denmark, S. E.; Hosoi, S. J. Org. Chem. 1994, 59, 5133. (e) Keck, G. E.; Dougherty, S. M.; Savin, K. A. J. Am. Chem. Soc. 1995, 117, 6210-6223. (f) Gevorgyan, V.; Kadota, I.; Yamamoto, Y. Tetrahedron Lett. 1993, 34, 1313. See also: Fleming, I Chemtracts 1991, 4, 21.
23. Allylsilanes: (a) Denmark, S. E.; Weber, E. J. Helv. Chim. Acta 1983, 66, 1655. (b) Denmark, S. E.; Weber, E. J.; Wilson, T. M.; Tetrahedron 1989, 45, 1053. (c) Mikami, K.; Maeda, T.; Kishi, N.; Nakai, T. Tetrahedron Lett. 1984, 25, 5151. Allylstannanes: (d) Denmark, S. E.; Hosoi, S. J. Org. Chem. 1994, 59, 5133. (e) Keck, G. E.; Dougherty, S. M.; Savin, K. A. J. Am. Chem. Soc. 1995, 117, 6210-6223. (f) Gevorgyan, V.; Kadota, I.; Yamamoto, Y. Tetrahedron Lett. 1993, 34, 1313. See also: Fleming, I Chemtracts 1991, 4, 21.
24. Allylsilanes: (a) Denmark, S. E.; Weber, E. J. Helv. Chim. Acta 1983, 66, 1655. (b) Denmark, S. E.; Weber, E. J.; Wilson, T. M.; Tetrahedron 1989, 45, 1053. (c) Mikami, K.; Maeda, T.; Kishi, N.; Nakai, T. Tetrahedron Lett. 1984, 25, 5151. Allylstannanes: (d) Denmark, S. E.; Hosoi, S. J. Org. Chem. 1994, 59, 5133. (e) Keck, G. E.; Dougherty, S. M.; Savin, K. A. J. Am. Chem. Soc. 1995, 117, 6210-6223. (f) Gevorgyan, V.; Kadota, I.; Yamamoto, Y. Tetrahedron Lett. 1993, 34, 1313. See also: Fleming, I Chemtracts 1991, 4, 21.
25. Allylsilanes: (a) Denmark, S. E.; Weber, E. J. Helv. Chim. Acta 1983, 66, 1655. (b) Denmark, S. E.; Weber, E. J.; Wilson, T. M.; Tetrahedron 1989, 45, 1053. (c) Mikami, K.; Maeda, T.; Kishi, N.; Nakai, T. Tetrahedron Lett. 1984, 25, 5151. Allylstannanes: (d) Denmark, S. E.; Hosoi, S. J. Org. Chem. 1994, 59, 5133. (e) Keck, G. E.; Dougherty, S. M.; Savin, K. A. J. Am. Chem. Soc. 1995, 117, 6210-6223. (f) Gevorgyan, V.; Kadota, I.; Yamamoto, Y. Tetrahedron Lett. 1993, 34, 1313. See also: Fleming, I Chemtracts 1991, 4, 21.
26. Allylsilanes: (a) Denmark, S. E.; Weber, E. J. Helv. Chim. Acta 1983, 66, 1655. (b) Denmark, S. E.; Weber, E. J.; Wilson, T. M.; Tetrahedron 1989, 45, 1053. (c) Mikami, K.; Maeda, T.; Kishi, N.; Nakai, T. Tetrahedron Lett. 1984, 25, 5151. Allylstannanes: (d) Denmark, S. E.; Hosoi, S. J. Org. Chem. 1994, 59, 5133. (e) Keck, G. E.; Dougherty, S. M.; Savin, K. A. J. Am. Chem. Soc. 1995, 117, 6210-6223. (f) Gevorgyan, V.; Kadota, I.; Yamamoto, Y. Tetrahedron Lett. 1993, 34, 1313. See also: Fleming, I Chemtracts 1991, 4, 21.
27. Allylstannanes: (a) Costa, A. L.; Piazza, M. G.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A. J. Am. Chem. Soc. 1993, 115, 7001. (b) Keck, G. E.; Tarbet, K. H.; Geraci, L. S. J. Am. Chem. Soc. 1993, 115, 8467. (c) Keck, G. E.; Krishnamurthy, D.; Grier, M. C. J. Org. Chem. 1993, 58, 6543. (d) Weigand, S.; Brukner, R. Chem. Eur. J. 1996, 2, 1072. (e) Bedeschi, P.; Casolari, S.; Costa, A. L.; Tagliavini, E.; Umani-Ronchi, A. Tetrahedron Lett. 1995, 36, 7897. (f) Yanagisawa, A.; Nakashima, H.; Ishiba, A.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 4723. (g) Yanagisawa, A.; Ishiba, A.; Nakashima, H.; Yamamoto, H. Synlett 1997, 88. Allylsilanes: (h) Hishihara, K.; Mouri, M.; Gao, Q.; Maruyama, T.; Furuta, K.; Yamamoto, H. J. Am. Chem. Soc. 1993, 115, 11490. (i) Carreira, E. M.; Gauthier, D. R., Jr. Angew. Chem., Int. Ed. Engl. 1996, 35, 2363.
28. Allylstannanes: (a) Costa, A. L.; Piazza, M. G.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A. J. Am. Chem. Soc. 1993, 115, 7001. (b) Keck, G. E.; Tarbet, K. H.; Geraci, L. S. J. Am. Chem. Soc. 1993, 115, 8467. (c) Keck, G. E.; Krishnamurthy, D.; Grier, M. C. J. Org. Chem. 1993, 58, 6543. (d) Weigand, S.; Brukner, R. Chem. Eur. J. 1996, 2, 1072. (e) Bedeschi, P.; Casolari, S.; Costa, A. L.; Tagliavini, E.; Umani-Ronchi, A. Tetrahedron Lett. 1995, 36, 7897. (f) Yanagisawa, A.; Nakashima, H.; Ishiba, A.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 4723. (g) Yanagisawa, A.; Ishiba, A.; Nakashima, H.; Yamamoto, H. Synlett 1997, 88. Allylsilanes: (h) Hishihara, K.; Mouri, M.; Gao, Q.; Maruyama, T.; Furuta, K.; Yamamoto, H. J. Am. Chem. Soc. 1993, 115, 11490. (i) Carreira, E. M.; Gauthier, D. R., Jr. Angew. Chem., Int. Ed. Engl. 1996, 35, 2363.
29. Allylstannanes: (a) Costa, A. L.; Piazza, M. G.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A. J. Am. Chem. Soc. 1993, 115, 7001. (b) Keck, G. E.; Tarbet, K. H.; Geraci, L. S. J. Am. Chem. Soc. 1993, 115, 8467. (c) Keck, G. E.; Krishnamurthy, D.; Grier, M. C. J. Org. Chem. 1993, 58, 6543. (d) Weigand, S.; Brukner, R. Chem. Eur. J. 1996, 2, 1072. (e) Bedeschi, P.; Casolari, S.; Costa, A. L.; Tagliavini, E.; Umani-Ronchi, A. Tetrahedron Lett. 1995, 36, 7897. (f) Yanagisawa, A.; Nakashima, H.; Ishiba, A.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 4723. (g) Yanagisawa, A.; Ishiba, A.; Nakashima, H.; Yamamoto, H. Synlett 1997, 88. Allylsilanes: (h) Hishihara, K.; Mouri, M.; Gao, Q.; Maruyama, T.; Furuta, K.; Yamamoto, H. J. Am. Chem. Soc. 1993, 115, 11490. (i) Carreira, E. M.; Gauthier, D. R., Jr. Angew. Chem., Int. Ed. Engl. 1996, 35, 2363.
30. Allylstannanes: (a) Costa, A. L.; Piazza, M. G.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A. J. Am. Chem. Soc. 1993, 115, 7001. (b) Keck, G. E.; Tarbet, K. H.; Geraci, L. S. J. Am. Chem. Soc. 1993, 115, 8467. (c) Keck, G. E.; Krishnamurthy, D.; Grier, M. C. J. Org. Chem. 1993, 58, 6543. (d) Weigand, S.; Brukner, R. Chem. Eur. J. 1996, 2, 1072. (e) Bedeschi, P.; Casolari, S.; Costa, A. L.; Tagliavini, E.; Umani-Ronchi, A. Tetrahedron Lett. 1995, 36, 7897. (f) Yanagisawa, A.; Nakashima, H.; Ishiba, A.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 4723. (g) Yanagisawa, A.; Ishiba, A.; Nakashima, H.; Yamamoto, H. Synlett 1997, 88. Allylsilanes: (h) Hishihara, K.; Mouri, M.; Gao, Q.; Maruyama, T.; Furuta, K.; Yamamoto, H. J. Am. Chem. Soc. 1993, 115, 11490. (i) Carreira, E. M.; Gauthier, D. R., Jr. Angew. Chem., Int. Ed. Engl. 1996, 35, 2363.
31. Allylstannanes: (a) Costa, A. L.; Piazza, M. G.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A. J. Am. Chem. Soc. 1993, 115, 7001. (b) Keck, G. E.; Tarbet, K. H.; Geraci, L. S. J. Am. Chem. Soc. 1993, 115, 8467. (c) Keck, G. E.; Krishnamurthy, D.; Grier, M. C. J. Org. Chem. 1993, 58, 6543. (d) Weigand, S.; Brukner, R. Chem. Eur. J. 1996, 2, 1072. (e) Bedeschi, P.; Casolari, S.; Costa, A. L.; Tagliavini, E.; Umani-Ronchi, A. Tetrahedron Lett. 1995, 36, 7897. (f) Yanagisawa, A.; Nakashima, H.; Ishiba, A.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 4723. (g) Yanagisawa, A.; Ishiba, A.; Nakashima, H.; Yamamoto, H. Synlett 1997, 88. Allylsilanes: (h) Hishihara, K.; Mouri, M.; Gao, Q.; Maruyama, T.; Furuta, K.; Yamamoto, H. J. Am. Chem. Soc. 1993, 115, 11490. (i) Carreira, E. M.; Gauthier, D. R., Jr. Angew. Chem., Int. Ed. Engl. 1996, 35, 2363.
32. Allylstannanes: (a) Costa, A. L.; Piazza, M. G.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A. J. Am. Chem. Soc. 1993, 115, 7001. (b) Keck, G. E.; Tarbet, K. H.; Geraci, L. S. J. Am. Chem. Soc. 1993, 115, 8467. (c) Keck, G. E.; Krishnamurthy, D.; Grier, M. C. J. Org. Chem. 1993, 58, 6543. (d) Weigand, S.; Brukner, R. Chem. Eur. J. 1996, 2, 1072. (e) Bedeschi, P.; Casolari, S.; Costa, A. L.; Tagliavini, E.; Umani-Ronchi, A. Tetrahedron Lett. 1995, 36, 7897. (f) Yanagisawa, A.; Nakashima, H.; Ishiba, A.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 4723. (g) Yanagisawa, A.; Ishiba, A.; Nakashima, H.; Yamamoto, H. Synlett 1997, 88. Allylsilanes: (h) Hishihara, K.; Mouri, M.; Gao, Q.; Maruyama, T.; Furuta, K.; Yamamoto, H. J. Am. Chem. Soc. 1993, 115, 11490. (i) Carreira, E. M.; Gauthier, D. R., Jr. Angew. Chem., Int. Ed. Engl. 1996, 35, 2363.
33. Allylstannanes: (a) Costa, A. L.; Piazza, M. G.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A. J. Am. Chem. Soc. 1993, 115, 7001. (b) Keck, G. E.; Tarbet, K. H.; Geraci, L. S. J. Am. Chem. Soc. 1993, 115, 8467. (c) Keck, G. E.; Krishnamurthy, D.; Grier, M. C. J. Org. Chem. 1993, 58, 6543. (d) Weigand, S.; Brukner, R. Chem. Eur. J. 1996, 2, 1072. (e) Bedeschi, P.; Casolari, S.; Costa, A. L.; Tagliavini, E.; Umani-Ronchi, A. Tetrahedron Lett. 1995, 36, 7897. (f) Yanagisawa, A.; Nakashima, H.; Ishiba, A.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 4723. (g) Yanagisawa, A.; Ishiba, A.; Nakashima, H.; Yamamoto, H. Synlett 1997, 88. Allylsilanes: (h) Hishihara, K.; Mouri, M.; Gao, Q.; Maruyama, T.; Furuta, K.; Yamamoto, H. J. Am. Chem. Soc. 1993, 115, 11490. (i) Carreira, E. M.; Gauthier, D. R., Jr. Angew. Chem., Int. Ed. Engl. 1996, 35, 2363.
34. Allylstannanes: (a) Costa, A. L.; Piazza, M. G.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A. J. Am. Chem. Soc. 1993, 115, 7001. (b) Keck, G. E.; Tarbet, K. H.; Geraci, L. S. J. Am. Chem. Soc. 1993, 115, 8467. (c) Keck, G. E.; Krishnamurthy, D.; Grier, M. C. J. Org. Chem. 1993, 58, 6543. (d) Weigand, S.; Brukner, R. Chem. Eur. J. 1996, 2, 1072. (e) Bedeschi, P.; Casolari, S.; Costa, A. L.; Tagliavini, E.; Umani-Ronchi, A. Tetrahedron Lett. 1995, 36, 7897. (f) Yanagisawa, A.; Nakashima, H.; Ishiba, A.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 4723. (g) Yanagisawa, A.; Ishiba, A.; Nakashima, H.; Yamamoto, H. Synlett 1997, 88. Allylsilanes: (h) Hishihara, K.; Mouri, M.; Gao, Q.; Maruyama, T.; Furuta, K.; Yamamoto, H. J. Am. Chem. Soc. 1993, 115, 11490. (i) Carreira, E. M.; Gauthier, D. R., Jr. Angew. Chem., Int. Ed. Engl. 1996, 35, 2363.
35. Allylstannanes: (a) Costa, A. L.; Piazza, M. G.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A. J. Am. Chem. Soc. 1993, 115, 7001. (b) Keck, G. E.; Tarbet, K. H.; Geraci, L. S. J. Am. Chem. Soc. 1993, 115, 8467. (c) Keck, G. E.; Krishnamurthy, D.; Grier, M. C. J. Org. Chem. 1993, 58, 6543. (d) Weigand, S.; Brukner, R. Chem. Eur. J. 1996, 2, 1072. (e) Bedeschi, P.; Casolari, S.; Costa, A. L.; Tagliavini, E.; Umani-Ronchi, A. Tetrahedron Lett. 1995, 36, 7897. (f) Yanagisawa, A.; Nakashima, H.; Ishiba, A.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 4723. (g) Yanagisawa, A.; Ishiba, A.; Nakashima, H.; Yamamoto, H. Synlett 1997, 88. Allylsilanes: (h) Hishihara, K.; Mouri, M.; Gao, Q.; Maruyama, T.; Furuta, K.; Yamamoto, H. J. Am. Chem. Soc. 1993, 115, 11490. (i) Carreira, E. M.; Gauthier, D. R., Jr. Angew. Chem., Int. Ed. Engl. 1996, 35, 2363.
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