Cyclic 1,2-diketones as building blocks for asymmetric synthesis of cycloalkenones [8]

Journal of the American Chemical Society

Volumn 122, Issue 15, 2000, Pages 3785-3786

  Trost, Barry M ^a   Schroeder, Gretchen M ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; CYCLOALKANONE; DIKETONE;

ALKYLATION; CATALYSIS; CATALYST; CHEMICAL REACTION; CYCLIZATION; DIASTEREOISOMER; ENANTIOMER; LETTER; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0034685525     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja000274m     Document Type: Letter

References (43)

1. For the synthesis of cyclic 1,2-diketones, see: (a) Hach, C. C.; Banks, C. V.; Diehl, H. Organic Syntheses; John Wiley & Sons: New York, 1963; Collect. Vol. IV, p 229. (b) Bauer, D. P.; Macomber, R. S. J. Org. Chem. 1970, 40, 1990. (c) Sato, K.; Inoue, S.; Ohashi, M. Bull. Chem. Soc. Jpn. 1974, 47, 2519. (d) Rao, D. V.; Stuber, F. A.; Ulrich, H. J. Org. Chem. 1979, 44, 456. (e) Utaka, M.; Matsushita, S.; Takeda, A. Chem. Lett. 1980, 779. (f) Vankar, Y. D.; Chaudhuri, N. C.; Rao, C. T. Tetrahedron Lett. 1987, 28, 551. (g) Trost, B. M.; Mikhail, G. K. J. Am. Chem. Soc. 1987, 109, 4124. (h) Kawada, K.; Gross, R. S.; Watt, D. S. Synth. Comm. 1989, 19, 777. (i) Horiuchi, C. A.; Kiyomiya, H.; Takahashi, M.; Suzuki, Y. Synthesis 1989, 10, 785. (j) Kanu, B. C.; Jana, U. J. Org. Chem. 1999, 64, 6380.
2. For the synthesis of cyclic 1,2-diketones, see: (a) Hach, C. C.; Banks, C. V.; Diehl, H. Organic Syntheses; John Wiley & Sons: New York, 1963; Collect. Vol. IV, p 229. (b) Bauer, D. P.; Macomber, R. S. J. Org. Chem. 1970, 40, 1990. (c) Sato, K.; Inoue, S.; Ohashi, M. Bull. Chem. Soc. Jpn. 1974, 47, 2519. (d) Rao, D. V.; Stuber, F. A.; Ulrich, H. J. Org. Chem. 1979, 44, 456. (e) Utaka, M.; Matsushita, S.; Takeda, A. Chem. Lett. 1980, 779. (f) Vankar, Y. D.; Chaudhuri, N. C.; Rao, C. T. Tetrahedron Lett. 1987, 28, 551. (g) Trost, B. M.; Mikhail, G. K. J. Am. Chem. Soc. 1987, 109, 4124. (h) Kawada, K.; Gross, R. S.; Watt, D. S. Synth. Comm. 1989, 19, 777. (i) Horiuchi, C. A.; Kiyomiya, H.; Takahashi, M.; Suzuki, Y. Synthesis 1989, 10, 785. (j) Kanu, B. C.; Jana, U. J. Org. Chem. 1999, 64, 6380.
3. For the synthesis of cyclic 1,2-diketones, see: (a) Hach, C. C.; Banks, C. V.; Diehl, H. Organic Syntheses; John Wiley & Sons: New York, 1963; Collect. Vol. IV, p 229. (b) Bauer, D. P.; Macomber, R. S. J. Org. Chem. 1970, 40, 1990. (c) Sato, K.; Inoue, S.; Ohashi, M. Bull. Chem. Soc. Jpn. 1974, 47, 2519. (d) Rao, D. V.; Stuber, F. A.; Ulrich, H. J. Org. Chem. 1979, 44, 456. (e) Utaka, M.; Matsushita, S.; Takeda, A. Chem. Lett. 1980, 779. (f) Vankar, Y. D.; Chaudhuri, N. C.; Rao, C. T. Tetrahedron Lett. 1987, 28, 551. (g) Trost, B. M.; Mikhail, G. K. J. Am. Chem. Soc. 1987, 109, 4124. (h) Kawada, K.; Gross, R. S.; Watt, D. S. Synth. Comm. 1989, 19, 777. (i) Horiuchi, C. A.; Kiyomiya, H.; Takahashi, M.; Suzuki, Y. Synthesis 1989, 10, 785. (j) Kanu, B. C.; Jana, U. J. Org. Chem. 1999, 64, 6380.
4. For the synthesis of cyclic 1,2-diketones, see: (a) Hach, C. C.; Banks, C. V.; Diehl, H. Organic Syntheses; John Wiley & Sons: New York, 1963; Collect. Vol. IV, p 229. (b) Bauer, D. P.; Macomber, R. S. J. Org. Chem. 1970, 40, 1990. (c) Sato, K.; Inoue, S.; Ohashi, M. Bull. Chem. Soc. Jpn. 1974, 47, 2519. (d) Rao, D. V.; Stuber, F. A.; Ulrich, H. J. Org. Chem. 1979, 44, 456. (e) Utaka, M.; Matsushita, S.; Takeda, A. Chem. Lett. 1980, 779. (f) Vankar, Y. D.; Chaudhuri, N. C.; Rao, C. T. Tetrahedron Lett. 1987, 28, 551. (g) Trost, B. M.; Mikhail, G. K. J. Am. Chem. Soc. 1987, 109, 4124. (h) Kawada, K.; Gross, R. S.; Watt, D. S. Synth. Comm. 1989, 19, 777. (i) Horiuchi, C. A.; Kiyomiya, H.; Takahashi, M.; Suzuki, Y. Synthesis 1989, 10, 785. (j) Kanu, B. C.; Jana, U. J. Org. Chem. 1999, 64, 6380.
5. For the synthesis of cyclic 1,2-diketones, see: (a) Hach, C. C.; Banks, C. V.; Diehl, H. Organic Syntheses; John Wiley & Sons: New York, 1963; Collect. Vol. IV, p 229. (b) Bauer, D. P.; Macomber, R. S. J. Org. Chem. 1970, 40, 1990. (c) Sato, K.; Inoue, S.; Ohashi, M. Bull. Chem. Soc. Jpn. 1974, 47, 2519. (d) Rao, D. V.; Stuber, F. A.; Ulrich, H. J. Org. Chem. 1979, 44, 456. (e) Utaka, M.; Matsushita, S.; Takeda, A. Chem. Lett. 1980, 779. (f) Vankar, Y. D.; Chaudhuri, N. C.; Rao, C. T. Tetrahedron Lett. 1987, 28, 551. (g) Trost, B. M.; Mikhail, G. K. J. Am. Chem. Soc. 1987, 109, 4124. (h) Kawada, K.; Gross, R. S.; Watt, D. S. Synth. Comm. 1989, 19, 777. (i) Horiuchi, C. A.; Kiyomiya, H.; Takahashi, M.; Suzuki, Y. Synthesis 1989, 10, 785. (j) Kanu, B. C.; Jana, U. J. Org. Chem. 1999, 64, 6380.
6. For the synthesis of cyclic 1,2-diketones, see: (a) Hach, C. C.; Banks, C. V.; Diehl, H. Organic Syntheses; John Wiley & Sons: New York, 1963; Collect. Vol. IV, p 229. (b) Bauer, D. P.; Macomber, R. S. J. Org. Chem. 1970, 40, 1990. (c) Sato, K.; Inoue, S.; Ohashi, M. Bull. Chem. Soc. Jpn. 1974, 47, 2519. (d) Rao, D. V.; Stuber, F. A.; Ulrich, H. J. Org. Chem. 1979, 44, 456. (e) Utaka, M.; Matsushita, S.; Takeda, A. Chem. Lett. 1980, 779. (f) Vankar, Y. D.; Chaudhuri, N. C.; Rao, C. T. Tetrahedron Lett. 1987, 28, 551. (g) Trost, B. M.; Mikhail, G. K. J. Am. Chem. Soc. 1987, 109, 4124. (h) Kawada, K.; Gross, R. S.; Watt, D. S. Synth. Comm. 1989, 19, 777. (i) Horiuchi, C. A.; Kiyomiya, H.; Takahashi, M.; Suzuki, Y. Synthesis 1989, 10, 785. (j) Kanu, B. C.; Jana, U. J. Org. Chem. 1999, 64, 6380.
7. For the synthesis of cyclic 1,2-diketones, see: (a) Hach, C. C.; Banks, C. V.; Diehl, H. Organic Syntheses; John Wiley & Sons: New York, 1963; Collect. Vol. IV, p 229. (b) Bauer, D. P.; Macomber, R. S. J. Org. Chem. 1970, 40, 1990. (c) Sato, K.; Inoue, S.; Ohashi, M. Bull. Chem. Soc. Jpn. 1974, 47, 2519. (d) Rao, D. V.; Stuber, F. A.; Ulrich, H. J. Org. Chem. 1979, 44, 456. (e) Utaka, M.; Matsushita, S.; Takeda, A. Chem. Lett. 1980, 779. (f) Vankar, Y. D.; Chaudhuri, N. C.; Rao, C. T. Tetrahedron Lett. 1987, 28, 551. (g) Trost, B. M.; Mikhail, G. K. J. Am. Chem. Soc. 1987, 109, 4124. (h) Kawada, K.; Gross, R. S.; Watt, D. S. Synth. Comm. 1989, 19, 777. (i) Horiuchi, C. A.; Kiyomiya, H.; Takahashi, M.; Suzuki, Y. Synthesis 1989, 10, 785. (j) Kanu, B. C.; Jana, U. J. Org. Chem. 1999, 64, 6380.
8. For the synthesis of cyclic 1,2-diketones, see: (a) Hach, C. C.; Banks, C. V.; Diehl, H. Organic Syntheses; John Wiley & Sons: New York, 1963; Collect. Vol. IV, p 229. (b) Bauer, D. P.; Macomber, R. S. J. Org. Chem. 1970, 40, 1990. (c) Sato, K.; Inoue, S.; Ohashi, M. Bull. Chem. Soc. Jpn. 1974, 47, 2519. (d) Rao, D. V.; Stuber, F. A.; Ulrich, H. J. Org. Chem. 1979, 44, 456. (e) Utaka, M.; Matsushita, S.; Takeda, A. Chem. Lett. 1980, 779. (f) Vankar, Y. D.; Chaudhuri, N. C.; Rao, C. T. Tetrahedron Lett. 1987, 28, 551. (g) Trost, B. M.; Mikhail, G. K. J. Am. Chem. Soc. 1987, 109, 4124. (h) Kawada, K.; Gross, R. S.; Watt, D. S. Synth. Comm. 1989, 19, 777. (i) Horiuchi, C. A.; Kiyomiya, H.; Takahashi, M.; Suzuki, Y. Synthesis 1989, 10, 785. (j) Kanu, B. C.; Jana, U. J. Org. Chem. 1999, 64, 6380.
9. For the synthesis of cyclic 1,2-diketones, see: (a) Hach, C. C.; Banks, C. V.; Diehl, H. Organic Syntheses; John Wiley & Sons: New York, 1963; Collect. Vol. IV, p 229. (b) Bauer, D. P.; Macomber, R. S. J. Org. Chem. 1970, 40, 1990. (c) Sato, K.; Inoue, S.; Ohashi, M. Bull. Chem. Soc. Jpn. 1974, 47, 2519. (d) Rao, D. V.; Stuber, F. A.; Ulrich, H. J. Org. Chem. 1979, 44, 456. (e) Utaka, M.; Matsushita, S.; Takeda, A. Chem. Lett. 1980, 779. (f) Vankar, Y. D.; Chaudhuri, N. C.; Rao, C. T. Tetrahedron Lett. 1987, 28, 551. (g) Trost, B. M.; Mikhail, G. K. J. Am. Chem. Soc. 1987, 109, 4124. (h) Kawada, K.; Gross, R. S.; Watt, D. S. Synth. Comm. 1989, 19, 777. (i) Horiuchi, C. A.; Kiyomiya, H.; Takahashi, M.; Suzuki, Y. Synthesis 1989, 10, 785. (j) Kanu, B. C.; Jana, U. J. Org. Chem. 1999, 64, 6380.
10. For the synthesis of cyclic 1,2-diketones, see: (a) Hach, C. C.; Banks, C. V.; Diehl, H. Organic Syntheses; John Wiley & Sons: New York, 1963; Collect. Vol. IV, p 229. (b) Bauer, D. P.; Macomber, R. S. J. Org. Chem. 1970, 40, 1990. (c) Sato, K.; Inoue, S.; Ohashi, M. Bull. Chem. Soc. Jpn. 1974, 47, 2519. (d) Rao, D. V.; Stuber, F. A.; Ulrich, H. J. Org. Chem. 1979, 44, 456. (e) Utaka, M.; Matsushita, S.; Takeda, A. Chem. Lett. 1980, 779. (f) Vankar, Y. D.; Chaudhuri, N. C.; Rao, C. T. Tetrahedron Lett. 1987, 28, 551. (g) Trost, B. M.; Mikhail, G. K. J. Am. Chem. Soc. 1987, 109, 4124. (h) Kawada, K.; Gross, R. S.; Watt, D. S. Synth. Comm. 1989, 19, 777. (i) Horiuchi, C. A.; Kiyomiya, H.; Takahashi, M.; Suzuki, Y. Synthesis 1989, 10, 785. (j) Kanu, B. C.; Jana, U. J. Org. Chem. 1999, 64, 6380.
11. For reviews of the palladium-catalyzed allylic alkylation reaction, see: (a) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395. (b) Heumann, A.; Reglier, M. Tetrahedron 1995, 51, 975. (c) Hayashi, T. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH Publishers Inc.; New York, 1993. (d) Sawamura, M.; Ito, Y. Chem. Rev. 1992, 92, 857. (e) Fiaud, J. C. In Metal- Promoted Selectivity in Organic Synthesis; Graziani, M., Hubert, A. J., Noels, A. F., Eds.; Kluwer Academic Publishers: Dordrecht, 1991. (f) Consiglio, G.; Waymouth, R. M. Chem. Rev. 1989, 89, 257.
12. For reviews of the palladium-catalyzed allylic alkylation reaction, see: (a) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395. (b) Heumann, A.; Reglier, M. Tetrahedron 1995, 51, 975. (c) Hayashi, T. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH Publishers Inc.; New York, 1993. (d) Sawamura, M.; Ito, Y. Chem. Rev. 1992, 92, 857. (e) Fiaud, J. C. In Metal- Promoted Selectivity in Organic Synthesis; Graziani, M., Hubert, A. J., Noels, A. F., Eds.; Kluwer Academic Publishers: Dordrecht, 1991. (f) Consiglio, G.; Waymouth, R. M. Chem. Rev. 1989, 89, 257.
13. For reviews of the palladium-catalyzed allylic alkylation reaction, see: (a) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395. (b) Heumann, A.; Reglier, M. Tetrahedron 1995, 51, 975. (c) Hayashi, T. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH Publishers Inc.; New York, 1993. (d) Sawamura, M.; Ito, Y. Chem. Rev. 1992, 92, 857. (e) Fiaud, J. C. In Metal- Promoted Selectivity in Organic Synthesis; Graziani, M., Hubert, A. J., Noels, A. F., Eds.; Kluwer Academic Publishers: Dordrecht, 1991. (f) Consiglio, G.; Waymouth, R. M. Chem. Rev. 1989, 89, 257.
14. For reviews of the palladium-catalyzed allylic alkylation reaction, see: (a) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395. (b) Heumann, A.; Reglier, M. Tetrahedron 1995, 51, 975. (c) Hayashi, T. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH Publishers Inc.; New York, 1993. (d) Sawamura, M.; Ito, Y. Chem. Rev. 1992, 92, 857. (e) Fiaud, J. C. In Metal- Promoted Selectivity in Organic Synthesis; Graziani, M., Hubert, A. J., Noels, A. F., Eds.; Kluwer Academic Publishers: Dordrecht, 1991. (f) Consiglio, G.; Waymouth, R. M. Chem. Rev. 1989, 89, 257.
15. For reviews of the palladium-catalyzed allylic alkylation reaction, see: (a) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395. (b) Heumann, A.; Reglier, M. Tetrahedron 1995, 51, 975. (c) Hayashi, T. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH Publishers Inc.; New York, 1993. (d) Sawamura, M.; Ito, Y. Chem. Rev. 1992, 92, 857. (e) Fiaud, J. C. In Metal-Promoted Selectivity in Organic Synthesis; Graziani, M., Hubert, A. J., Noels, A. F., Eds.; Kluwer Academic Publishers: Dordrecht, 1991. (f) Consiglio, G.; Waymouth, R. M. Chem. Rev. 1989, 89, 257.
16. For reviews of the palladium-catalyzed allylic alkylation reaction, see: (a) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395. (b) Heumann, A.; Reglier, M. Tetrahedron 1995, 51, 975. (c) Hayashi, T. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH Publishers Inc.; New York, 1993. (d) Sawamura, M.; Ito, Y. Chem. Rev. 1992, 92, 857. (e) Fiaud, J. C. In Metal- Promoted Selectivity in Organic Synthesis; Graziani, M., Hubert, A. J., Noels, A. F., Eds.; Kluwer Academic Publishers: Dordrecht, 1991. (f) Consiglio, G.; Waymouth, R. M. Chem. Rev. 1989, 89, 257.
17. For reviews of the Claisen rearrangement, see: (a) Ito, H.; Taguchi, T. Chem. Soc. Rev. 1999, 28, 43. (b) Gaweski, J. J. Acc. Chem. Res. 1997, 30, 219. (c) Ganem, B. Angew. Chem., Int. Ed. Engl. 1996, 35, 936. (d) P. Wipf in, Comprehensive Organic Synthesis ed. B. M. Trost and I. Fleming, Pergamon Press: Oxford, 1991, vol 5, 827. (e) Ziegler, F. E. Chem. Rev. 1988, 88, 1423. (f) Rhoads, S. J.; Rawlins, N. R. Org. React. 1915, 22, 1.
18. For reviews of the Claisen rearrangement, see: (a) Ito, H.; Taguchi, T. Chem. Soc. Rev. 1999, 28, 43. (b) Gaweski, J. J. Acc. Chem. Res. 1997, 30, 219. (c) Ganem, B. Angew. Chem., Int. Ed. Engl. 1996, 35, 936. (d) P. Wipf in, Comprehensive Organic Synthesis ed. B. M. Trost and I. Fleming, Pergamon Press: Oxford, 1991, vol 5, 827. (e) Ziegler, F. E. Chem. Rev. 1988, 88, 1423. (f) Rhoads, S. J.; Rawlins, N. R. Org. React. 1915, 22, 1.
19. For reviews of the Claisen rearrangement, see: (a) Ito, H.; Taguchi, T. Chem. Soc. Rev. 1999, 28, 43. (b) Gaweski, J. J. Acc. Chem. Res. 1997, 30, 219. (c) Ganem, B. Angew. Chem., Int. Ed. Engl. 1996, 35, 936. (d) P. Wipf in, Comprehensive Organic Synthesis ed. B. M. Trost and I. Fleming, Pergamon Press: Oxford, 1991, vol 5, 827. (e) Ziegler, F. E. Chem. Rev. 1988, 88, 1423. (f) Rhoads, S. J.; Rawlins, N. R. Org. React. 1915, 22, 1.
20. For reviews of the Claisen rearrangement, see: (a) Ito, H.; Taguchi, T. Chem. Soc. Rev. 1999, 28, 43. (b) Gaweski, J. J. Acc. Chem. Res. 1997, 30, 219. (c) Ganem, B. Angew. Chem., Int. Ed. Engl. 1996, 35, 936. (d) P. Wipf in, Comprehensive Organic Synthesis ed. B. M. Trost and I. Fleming, Pergamon Press: Oxford, 1991, vol 5, 827. (e) Ziegler, F. E. Chem. Rev. 1988, 88, 1423. (f) Rhoads, S. J.; Rawlins, N. R. Org. React. 1915, 22, 1.
21. For reviews of the Claisen rearrangement, see: (a) Ito, H.; Taguchi, T. Chem. Soc. Rev. 1999, 28, 43. (b) Gaweski, J. J. Acc. Chem. Res. 1997, 30, 219. (c) Ganem, B. Angew. Chem., Int. Ed. Engl. 1996, 35, 936. (d) P. Wipf in, Comprehensive Organic Synthesis ed. B. M. Trost and I. Fleming, Pergamon Press: Oxford, 1991, vol 5, 827. (e) Ziegler, F. E. Chem. Rev. 1988, 88, 1423. (f) Rhoads, S. J.; Rawlins, N. R. Org. React. 1915, 22, 1.
22. For reviews of the Claisen rearrangement, see: (a) Ito, H.; Taguchi, T. Chem. Soc. Rev. 1999, 28, 43. (b) Gaweski, J. J. Acc. Chem. Res. 1997, 30, 219. (c) Ganem, B. Angew. Chem., Int. Ed. Engl. 1996, 35, 936. (d) P. Wipf in, Comprehensive Organic Synthesis ed. B. M. Trost and I. Fleming, Pergamon Press: Oxford, 1991, vol 5, 827. (e) Ziegler, F. E. Chem. Rev. 1988, 88, 1423. (f) Rhoads, S. J.; Rawlins, N. R. Org. React. 1915, 22, 1.
23. For examples of Claisen rearrangements of cyclic 1,2-diketones, see: (a) Ponaras, A. A. J. Org. Chem. 1983, 48, 3866. (b) Ponaras, A. A. Tetrahedron Lett. 1983, 24, 3. (c) Dauben, W. G.; Ponaras, A. A.; Chollet, A. J. Org. Chem. 1980, 45, 4413, (d) Ponaras, A. A. Tetrahedron Lett. 1980, 21, 4803.
24. For examples of Claisen rearrangements of cyclic 1,2-diketones, see: (a) Ponaras, A. A. J. Org. Chem. 1983, 48, 3866. (b) Ponaras, A. A. Tetrahedron Lett. 1983, 24, 3. (c) Dauben, W. G.; Ponaras, A. A.; Chollet, A. J. Org. Chem. 1980, 45, 4413, (d) Ponaras, A. A. Tetrahedron Lett. 1980, 21, 4803.
25. For examples of Claisen rearrangements of cyclic 1,2-diketones, see: (a) Ponaras, A. A. J. Org. Chem. 1983, 48, 3866. (b) Ponaras, A. A. Tetrahedron Lett. 1983, 24, 3. (c) Dauben, W. G.; Ponaras, A. A.; Chollet, A. J. Org. Chem. 1980, 45, 4413, (d) Ponaras, A. A. Tetrahedron Lett. 1980, 21, 4803.
26. For examples of Claisen rearrangements of cyclic 1,2-diketones, see: (a) Ponaras, A. A. J. Org. Chem. 1983, 48, 3866. (b) Ponaras, A. A. Tetrahedron Lett. 1983, 24, 3. (c) Dauben, W. G.; Ponaras, A. A.; Chollet, A. J. Org. Chem. 1980, 45, 4413, (d) Ponaras, A. A. Tetrahedron Lett. 1980, 21, 4803.
27. The palladium-catalyzed asymmetric O-alkylation of phenols and Claisen rearrangement of the resulting allyl aryl ethers was recently reported. (a) Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 1998, 120, 815, (b) Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 1998, 120, 9074.
28. The palladium-catalyzed asymmetric O-alkylation of phenols and Claisen rearrangement of the resulting allyl aryl ethers was recently reported. (a) Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 1998, 120, 815, (b) Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 1998, 120, 9074.
29. (a) Trost, B. M.; Van Vranken, D. L.; Bingel, C. J. Am. Chem. Soc. 1992, 114, 9327.
30. (b) Trost, B. M.; Bunt, R. C. Angew. Chem., Int. Ed. Engl. 1996, 35, 99.
31. The absolute configuration shown in eq 2 was assigned by applying the mnemonic developed in the group for the palladium-catalyzed asymmetric allylic alkylation reaction using ligands 4 and 5 (see ref 2a and 6a).
32. The absolute configuration shown in eqs 3 and 4 was assigned by comparison of the optical rotation of a derivative to that reported in the literature.
33. For recent papers on controlling the regiochemislry of Pd-catalyzed allylic alkylations, see: (a) Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 1999, 121, 4545. (b) Pretot, R.; Pfaltz, A. Angew. Chem., Int. Ed. 1998, 37, 323. (c) Hayashi, T.; Kawatsura, H.; Uozumi, Y. J. Am. Chem. Soc. 1998, 120, 1681.
34. For recent papers on controlling the regiochemislry of Pd-catalyzed allylic alkylations, see: (a) Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 1999, 121, 4545. (b) Pretot, R.; Pfaltz, A. Angew. Chem., Int. Ed. 1998, 37, 323. (c) Hayashi, T.; Kawatsura, H.; Uozumi, Y. J. Am. Chem. Soc. 1998, 120, 1681.
35. For recent papers on controlling the regiochemislry of Pd-catalyzed allylic alkylations, see: (a) Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 1999, 121, 4545. (b) Pretot, R.; Pfaltz, A. Angew. Chem., Int. Ed. 1998, 37, 323. (c) Hayashi, T.; Kawatsura, H.; Uozumi, Y. J. Am. Chem. Soc. 1998, 120, 1681.
36. Trost, B. M.; Verhoeven, T. R. J. Am. Chem. Soc. 1980, 102, 4730.
37. Trost, B. M.; McEachern, E. J.; Toste, F. D. J. Am. Chem. Soc. 1998, 120, 12702.
38. The absolute stereochemistry was assigned in analogy to previous work, see: ref 6b.
39. Imamoto, T. In Lanthanides in Organic Synthesis; Academic Press: London, U. K., 1994; Chapter 5, pp 67-118.
40. Chirality transfer is defined as (% ee product/% ee starting material) × 100%. In reporting ee's, the first number in parentheses is the observed ee of the product and the second represents this number corrected for the ee of the starting material.
41. For a recent review of triflate chemistry, see: Ritter, K. Synthesis 1993, 735.
42. Gacchi, S.; Morera, E.; Ortar, G. Tetrahedron Lett. 1984, 25, 4821.
43. Ciattini, P. G.; Morera, E.; Ortar, G. Tetrahedron Lett. 1992, 33, 4815.