The First Stereoselective Ficini-Claisen Rearrangement Using Chiral Ynamides

Organic Letters

Volumn 4, Issue 8, 2002, Pages 1383-1386

  Mulder, Jason A ^a   Hsung, Richard P ^a   Frederick, Michael O ^a,b   Tracey, Michael R ^a   Zificsak, Craig A ^a  

^a University of Minnesota   (United States)

^b UMN Heisig Summer Undergraduate ^*

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE;

EID: 0000967977     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol020037j     Document Type: Article

References (81)

1. For reviews on chemistry of ynamines see: (a) Zificsak, C. A.; Mulder, J. A.; Hsung, R. P.; Rameshkumar, C.; Wei, L.-L. Tetrahedron 2001, 57, 7575. (b) Himbert, G. In Methoden Der Organischen Chemie (Houben-Weyl); Kropf, H., Schaumann, E., Eds.; Georg Thieme Verlag: Stuttgart, 1993; pp 3267-3443. (c) Collard-Motte, J.; Janousek, Z. Top. Curr. Chem. 1986, 130, 89. (d) Ficini, J. Tetrahedron 1976, 32, 1448. (e) Viehe, H. G. Chemistry of Acetylenes, Ynamines; Marcel Dekker: New York, 1969.
2. For reviews on chemistry of ynamines see: (a) Zificsak, C. A.; Mulder, J. A.; Hsung, R. P.; Rameshkumar, C.; Wei, L.-L. Tetrahedron 2001, 57, 7575. (b) Himbert, G. In Methoden Der Organischen Chemie (Houben-Weyl); Kropf, H., Schaumann, E., Eds.; Georg Thieme Verlag: Stuttgart, 1993; pp 3267-3443. (c) Collard-Motte, J.; Janousek, Z. Top. Curr. Chem. 1986, 130, 89. (d) Ficini, J. Tetrahedron 1976, 32, 1448. (e) Viehe, H. G. Chemistry of Acetylenes, Ynamines; Marcel Dekker: New York, 1969.
3. For reviews on chemistry of ynamines see: (a) Zificsak, C. A.; Mulder, J. A.; Hsung, R. P.; Rameshkumar, C.; Wei, L.-L. Tetrahedron 2001, 57, 7575. (b) Himbert, G. In Methoden Der Organischen Chemie (Houben-Weyl); Kropf, H., Schaumann, E., Eds.; Georg Thieme Verlag: Stuttgart, 1993; pp 3267-3443. (c) Collard-Motte, J.; Janousek, Z. Top. Curr. Chem. 1986, 130, 89. (d) Ficini, J. Tetrahedron 1976, 32, 1448. (e) Viehe, H. G. Chemistry of Acetylenes, Ynamines; Marcel Dekker: New York, 1969.
4. For reviews on chemistry of ynamines see: (a) Zificsak, C. A.; Mulder, J. A.; Hsung, R. P.; Rameshkumar, C.; Wei, L.-L. Tetrahedron 2001, 57, 7575. (b) Himbert, G. In Methoden Der Organischen Chemie (Houben-Weyl); Kropf, H., Schaumann, E., Eds.; Georg Thieme Verlag: Stuttgart, 1993; pp 3267-3443. (c) Collard-Motte, J.; Janousek, Z. Top. Curr. Chem. 1986, 130, 89. (d) Ficini, J. Tetrahedron 1976, 32, 1448. (e) Viehe, H. G. Chemistry of Acetylenes, Ynamines; Marcel Dekker: New York, 1969.
5. For reviews on chemistry of ynamines see: (a) Zificsak, C. A.; Mulder, J. A.; Hsung, R. P.; Rameshkumar, C.; Wei, L.-L. Tetrahedron 2001, 57, 7575. (b) Himbert, G. In Methoden Der Organischen Chemie (Houben-Weyl); Kropf, H., Schaumann, E., Eds.; Georg Thieme Verlag: Stuttgart, 1993; pp 3267-3443. (c) Collard-Motte, J.; Janousek, Z. Top. Curr. Chem. 1986, 130, 89. (d) Ficini, J. Tetrahedron 1976, 32, 1448. (e) Viehe, H. G. Chemistry of Acetylenes, Ynamines; Marcel Dekker: New York, 1969.
6. (a) Wei, L.-L.; Mulder, J. A.; Xiong, H.; Zificsak, C. A.; Douglas, C. J.; Hsung, R. P. Tetrahedron 2001, 57, 459-466.
7. (b) Hsung, R. P.; Zificsak, C. A.; Wei, L.-L.; Douglas, C. J.; Xiong, H.; Mulder, J. A. Org. Lett. 1999, 1, 1237.
8. For chemistry of allenamides, see: (a) Xiong, H.; Hsung. R. P.; Berry, C. R.; Rameshkumar, C. J. Am. Chem. Soc. 2001, 123, 7174. (b) Xiong, H.; Hsung, R. P.; Wei, L.-L.; Berry, C. R.; Mulder, J. A.; Stockwell, B. Org. Lett. 2000, 2, 2869. (c) Wei, L.-L.; Hsung, R. P.; Xiong, H.; Mulder, J. A.; Nkansah, N. T. Org. Lett. 1999, 1, 2145. (d) Wei, L.-L.; Xiong, H.; Douglas, C. J.; Hsung, R. P. Tetrahedron Lett. 1999, 40, 6903.
9. For chemistry of allenamides, see: (a) Xiong, H.; Hsung. R. P.; Berry, C. R.; Rameshkumar, C. J. Am. Chem. Soc. 2001, 123, 7174. (b) Xiong, H.; Hsung, R. P.; Wei, L.-L.; Berry, C. R.; Mulder, J. A.; Stockwell, B. Org. Lett. 2000, 2, 2869. (c) Wei, L.-L.; Hsung, R. P.; Xiong, H.; Mulder, J. A.; Nkansah, N. T. Org. Lett. 1999, 1, 2145. (d) Wei, L.-L.; Xiong, H.; Douglas, C. J.; Hsung, R. P. Tetrahedron Lett. 1999, 40, 6903.
10. For chemistry of allenamides, see: (a) Xiong, H.; Hsung. R. P.; Berry, C. R.; Rameshkumar, C. J. Am. Chem. Soc. 2001, 123, 7174. (b) Xiong, H.; Hsung, R. P.; Wei, L.-L.; Berry, C. R.; Mulder, J. A.; Stockwell, B. Org. Lett. 2000, 2, 2869. (c) Wei, L.-L.; Hsung, R. P.; Xiong, H.; Mulder, J. A.; Nkansah, N. T. Org. Lett. 1999, 1, 2145. (d) Wei, L.-L.; Xiong, H.; Douglas, C. J.; Hsung, R. P. Tetrahedron Lett. 1999, 40, 6903.
11. For chemistry of allenamides, see: (a) Xiong, H.; Hsung. R. P.; Berry, C. R.; Rameshkumar, C. J. Am. Chem. Soc. 2001, 123, 7174. (b) Xiong, H.; Hsung, R. P.; Wei, L.-L.; Berry, C. R.; Mulder, J. A.; Stockwell, B. Org. Lett. 2000, 2, 2869. (c) Wei, L.-L.; Hsung, R. P.; Xiong, H.; Mulder, J. A.; Nkansah, N. T. Org. Lett. 1999, 1, 2145. (d) Wei, L.-L.; Xiong, H.; Douglas, C. J.; Hsung, R. P. Tetrahedron Lett. 1999, 40, 6903.
12. For the first examples of ynamides, see: (a) Janousek, Z.; Collard, J.; Viehe, H. G. Angew. Chem., Int. Ed. Engl. 1972, 11, 917. (b) Goffin, E.; Legrand, Y.; Viehe, H. G. J. Chem. Res., Synop. 1977, 105.
13. For the first examples of ynamides, see: (a) Janousek, Z.; Collard, J.; Viehe, H. G. Angew. Chem., Int. Ed. Engl. 1972, 11, 917. (b) Goffin, E.; Legrand, Y.; Viehe, H. G. J. Chem. Res., Synop. 1977, 105.
14. For other recent examples, see: (a) Brückner, D. Synlett 2000, 1402. (b) Fromont, C.; Masson, S. Tetrahedron 1999, 55, 5405. (c) Feldman, K. S.; Bruendl, M. M.; Schildknegt, K.; Bohnstedt, A. C. J. Org. Chem. 1996, 61, 5440. (d) Joshi, R V.; Xu, Z.-Q.; Ksebati, M. B.; Kessel, D.; Corbett, T. H.; Drach, J. C.; Zemlicka, J. J. Chem. Soc., Perkin Trans. 1 1994, 1089. (e) Novikov, M. S.; Khlebnikov, A. F.; Kostikov, R. R. J. Org. Chem. USSR 1991, 27, 1576. (f) Tikhomirov, D. A.; Eremeev, A. V. Chem. Heterocycl. Comput. 1987, 23, 1141. (g) Balsamo, A.; Macchia, B.; Macchia, F.; Rossello, A. Tetrahedron Lett. 1985, 26, 4141.
15. For other recent examples, see: (a) Brückner, D. Synlett 2000, 1402. (b) Fromont, C.; Masson, S. Tetrahedron 1999, 55, 5405. (c) Feldman, K. S.; Bruendl, M. M.; Schildknegt, K.; Bohnstedt, A. C. J. Org. Chem. 1996, 61, 5440. (d) Joshi, R V.; Xu, Z.-Q.; Ksebati, M. B.; Kessel, D.; Corbett, T. H.; Drach, J. C.; Zemlicka, J. J. Chem. Soc., Perkin Trans. 1 1994, 1089. (e) Novikov, M. S.; Khlebnikov, A. F.; Kostikov, R. R. J. Org. Chem. USSR 1991, 27, 1576. (f) Tikhomirov, D. A.; Eremeev, A. V. Chem. Heterocycl. Comput. 1987, 23, 1141. (g) Balsamo, A.; Macchia, B.; Macchia, F.; Rossello, A. Tetrahedron Lett. 1985, 26, 4141.
16. For other recent examples, see: (a) Brückner, D. Synlett 2000, 1402. (b) Fromont, C.; Masson, S. Tetrahedron 1999, 55, 5405. (c) Feldman, K. S.; Bruendl, M. M.; Schildknegt, K.; Bohnstedt, A. C. J. Org. Chem. 1996, 61, 5440. (d) Joshi, R V.; Xu, Z.-Q.; Ksebati, M. B.; Kessel, D.; Corbett, T. H.; Drach, J. C.; Zemlicka, J. J. Chem. Soc., Perkin Trans. 1 1994, 1089. (e) Novikov, M. S.; Khlebnikov, A. F.; Kostikov, R. R. J. Org. Chem. USSR 1991, 27, 1576. (f) Tikhomirov, D. A.; Eremeev, A. V. Chem. Heterocycl. Comput. 1987, 23, 1141. (g) Balsamo, A.; Macchia, B.; Macchia, F.; Rossello, A. Tetrahedron Lett. 1985, 26, 4141.
17. For other recent examples, see: (a) Brückner, D. Synlett 2000, 1402. (b) Fromont, C.; Masson, S. Tetrahedron 1999, 55, 5405. (c) Feldman, K. S.; Bruendl, M. M.; Schildknegt, K.; Bohnstedt, A. C. J. Org. Chem. 1996, 61, 5440. (d) Joshi, R V.; Xu, Z.-Q.; Ksebati, M. B.; Kessel, D.; Corbett, T. H.; Drach, J. C.; Zemlicka, J. J. Chem. Soc., Perkin Trans. 1 1994, 1089. (e) Novikov, M. S.; Khlebnikov, A. F.; Kostikov, R. R. J. Org. Chem. USSR 1991, 27, 1576. (f) Tikhomirov, D. A.; Eremeev, A. V. Chem. Heterocycl. Comput. 1987, 23, 1141. (g) Balsamo, A.; Macchia, B.; Macchia, F.; Rossello, A. Tetrahedron Lett. 1985, 26, 4141.
18. For other recent examples, see: (a) Brückner, D. Synlett 2000, 1402. (b) Fromont, C.; Masson, S. Tetrahedron 1999, 55, 5405. (c) Feldman, K. S.; Bruendl, M. M.; Schildknegt, K.; Bohnstedt, A. C. J. Org. Chem. 1996, 61, 5440. (d) Joshi, R V.; Xu, Z.-Q.; Ksebati, M. B.; Kessel, D.; Corbett, T. H.; Drach, J. C.; Zemlicka, J. J. Chem. Soc., Perkin Trans. 1 1994, 1089. (e) Novikov, M. S.; Khlebnikov, A. F.; Kostikov, R. R. J. Org. Chem. USSR 1991, 27, 1576. (f) Tikhomirov, D. A.; Eremeev, A. V. Chem. Heterocycl. Comput. 1987, 23, 1141. (g) Balsamo, A.; Macchia, B.; Macchia, F.; Rossello, A. Tetrahedron Lett. 1985, 26, 4141.
19. For other recent examples, see: (a) Brückner, D. Synlett 2000, 1402. (b) Fromont, C.; Masson, S. Tetrahedron 1999, 55, 5405. (c) Feldman, K. S.; Bruendl, M. M.; Schildknegt, K.; Bohnstedt, A. C. J. Org. Chem. 1996, 61, 5440. (d) Joshi, R V.; Xu, Z.-Q.; Ksebati, M. B.; Kessel, D.; Corbett, T. H.; Drach, J. C.; Zemlicka, J. J. Chem. Soc., Perkin Trans. 1 1994, 1089. (e) Novikov, M. S.; Khlebnikov, A. F.; Kostikov, R. R. J. Org. Chem. USSR 1991, 27, 1576. (f) Tikhomirov, D. A.; Eremeev, A. V. Chem. Heterocycl. Comput. 1987, 23, 1141. (g) Balsamo, A.; Macchia, B.; Macchia, F.; Rossello, A. Tetrahedron Lett. 1985, 26, 4141.
20. For other recent examples, see: (a) Brückner, D. Synlett 2000, 1402. (b) Fromont, C.; Masson, S. Tetrahedron 1999, 55, 5405. (c) Feldman, K. S.; Bruendl, M. M.; Schildknegt, K.; Bohnstedt, A. C. J. Org. Chem. 1996, 61, 5440. (d) Joshi, R V.; Xu, Z.-Q.; Ksebati, M. B.; Kessel, D.; Corbett, T. H.; Drach, J. C.; Zemlicka, J. J. Chem. Soc., Perkin Trans. 1 1994, 1089. (e) Novikov, M. S.; Khlebnikov, A. F.; Kostikov, R. R. J. Org. Chem. USSR 1991, 27, 1576. (f) Tikhomirov, D. A.; Eremeev, A. V. Chem. Heterocycl. Comput. 1987, 23, 1141. (g) Balsamo, A.; Macchia, B.; Macchia, F.; Rossello, A. Tetrahedron Lett. 1985, 26, 4141.
21. (a) Zaugg, H. E.; Swett, L. R.; Stone, G. R. J. Org. Chem. 1958, 23, 1389.
22. (b) Katritzky, A. R.; Ramer, W. H. J. Org. Chem. 1985, 50, 852.
23. (a) Rainier, J. D.; Imbriglio, J. E. J. Org. Chem. 2000, 65, 7272.
24. (b) Rainier, J. D.; Imbriglio, J. E. Org. Lett. 1999, 1, 2037.
25. (a) Witulski, B.; Stengel, T. Angew. Chem., Int. Ed. 1998, 37, 489.
26. (b) Witulski, B.; Stengel, T. Angew. Chem., Int. Ed. 1998, 38, 2426.
27. (c) Witulski, B.; Gössmann, M. Chem. Commun. 1999, 1879.
28. (d) Witulski, B.; Gössmann, M. Synlett 2000, 1793.
29. (e) Witulski, B.; Buschmann, N.; Bergsträsser, U. Tetrahedron 2000, 56, 8473.
30. (f) Witulski, B.; Stengel, T.; Fernàndez-Hernàndez, J. M. Chem. Commun. 2000, 1965.
31. (a) Schottelius, M. J.; Chen, P. Helv. Chim. Acta 1998, 81, 2341.
32. (b) Suzuki, A. J. Organomet. Chem. 1999, 576, 147.
33. (c) Miyaura, M.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
34. (a) Claisen, L. Ber. Dtsch. Chem. Ges. 1912, 45, 3157.
35. For other major variations, see: (b) Carroll, M. F. J. Chem. Soc. 1940, 704.
36. (c) Wick, A. E.; Felix, D.; Steen, K.; Eschenmoser, A. Helv. Chim. Acta 1964, 47, 2425.
37. (d) Johnson, W. S.; Werthemann, L.; Bartlett, W. R.; Brocksom, T. J.; Li, T.-T.; Faulkner, D. J.; Petersen, M. R. J. Am. Chem. Soc. 1970, 92, 741.
38. (e) Ireland, R. E.; Mueller, R. H. J. Am. Chem. Soc. 1972, 94, 5897.
39. (a) Wipf, P. In Comprehensive Organic Synthesis, Vol. 5, Trost, B. M., Fleming, I., Eds. Pergamon Press: Oxford, 1991, 827.
40. b) Frauenrath, H. in Methoden Der Organischen Chemie (Houben-Weyl), Kiopf, H. and Schaumann, E., Eds. Georg Thieme Verlag: Stuttgart, 1995, p3301.
41. (c) Hill, R. K. in Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984.
42. (d) Gajewski, J. J. Hydrocarbon Thermal Isomerizations; Academic Press: New York, 1981.
43. Also see: (a) Ito, H.; Taguchi, T. Chem. Soc. Rev. 1999, 28, 43. (b) Enders, D.; Knopp, M.; Schiffers, R. Tetrahedron: Asymmetry 1996, 7, 1847. (c) Blechert, S. Synthesis 1989, 71. (d) Kallmerten, J.; Wittman, M. D. Stud. Nat. Prod. Chem. 1989, 3, 233. (e) Ziegler, F. E. Chem. Rev. 1988, 88, 1423. (f) Murray, A. W. Org. React. Mech. 1987, 457; Org. React. Mech. 1986, 429. (g) Moody, C. J. Adv. Heterocycl. Chem. 1987, 42, 203. (h) Barlett, P. A. Tetrahedron 1980, 36, 3. (i) Lutz, R. P. Chem. Rev. 1984, 84, 205. (j) Rhoads, S. J.; Raulins, N. R. Org. React. 1975, 1.
44. Also see: (a) Ito, H.; Taguchi, T. Chem. Soc. Rev. 1999, 28, 43. (b) Enders, D.; Knopp, M.; Schiffers, R. Tetrahedron: Asymmetry 1996, 7, 1847. (c) Blechert, S. Synthesis 1989, 71. (d) Kallmerten, J.; Wittman, M. D. Stud. Nat. Prod. Chem. 1989, 3, 233. (e) Ziegler, F. E. Chem. Rev. 1988, 88, 1423. (f) Murray, A. W. Org. React. Mech. 1987, 457; Org. React. Mech. 1986, 429. (g) Moody, C. J. Adv. Heterocycl. Chem. 1987, 42, 203. (h) Barlett, P. A. Tetrahedron 1980, 36, 3. (i) Lutz, R. P. Chem. Rev. 1984, 84, 205. (j) Rhoads, S. J.; Raulins, N. R. Org. React. 1975, 1.
45. Also see: (a) Ito, H.; Taguchi, T. Chem. Soc. Rev. 1999, 28, 43. (b) Enders, D.; Knopp, M.; Schiffers, R. Tetrahedron: Asymmetry 1996, 7, 1847. (c) Blechert, S. Synthesis 1989, 71. (d) Kallmerten, J.; Wittman, M. D. Stud. Nat. Prod. Chem. 1989, 3, 233. (e) Ziegler, F. E. Chem. Rev. 1988, 88, 1423. (f) Murray, A. W. Org. React. Mech. 1987, 457; Org. React. Mech. 1986, 429. (g) Moody, C. J. Adv. Heterocycl. Chem. 1987, 42, 203. (h) Barlett, P. A. Tetrahedron 1980, 36, 3. (i) Lutz, R. P. Chem. Rev. 1984, 84, 205. (j) Rhoads, S. J.; Raulins, N. R. Org. React. 1975, 1.
46. Also see: (a) Ito, H.; Taguchi, T. Chem. Soc. Rev. 1999, 28, 43. (b) Enders, D.; Knopp, M.; Schiffers, R. Tetrahedron: Asymmetry 1996, 7, 1847. (c) Blechert, S. Synthesis 1989, 71. (d) Kallmerten, J.; Wittman, M. D. Stud. Nat. Prod. Chem. 1989, 3, 233. (e) Ziegler, F. E. Chem. Rev. 1988, 88, 1423. (f) Murray, A. W. Org. React. Mech. 1987, 457; Org. React. Mech. 1986, 429. (g) Moody, C. J. Adv. Heterocycl. Chem. 1987, 42, 203. (h) Barlett, P. A. Tetrahedron 1980, 36, 3. (i) Lutz, R. P. Chem. Rev. 1984, 84, 205. (j) Rhoads, S. J.; Raulins, N. R. Org. React. 1975, 1.
47. Also see: (a) Ito, H.; Taguchi, T. Chem. Soc. Rev. 1999, 28, 43. (b) Enders, D.; Knopp, M.; Schiffers, R. Tetrahedron: Asymmetry 1996, 7, 1847. (c) Blechert, S. Synthesis 1989, 71. (d) Kallmerten, J.; Wittman, M. D. Stud. Nat. Prod. Chem. 1989, 3, 233. (e) Ziegler, F. E. Chem. Rev. 1988, 88, 1423. (f) Murray, A. W. Org. React. Mech. 1987, 457; Org. React. Mech. 1986, 429. (g) Moody, C. J. Adv. Heterocycl. Chem. 1987, 42, 203. (h) Barlett, P. A. Tetrahedron 1980, 36, 3. (i) Lutz, R. P. Chem. Rev. 1984, 84, 205. (j) Rhoads, S. J.; Raulins, N. R. Org. React. 1975, 1.
48. Also see: (a) Ito, H.; Taguchi, T. Chem. Soc. Rev. 1999, 28, 43. (b) Enders, D.; Knopp, M.; Schiffers, R. Tetrahedron: Asymmetry 1996, 7, 1847. (c) Blechert, S. Synthesis 1989, 71. (d) Kallmerten, J.; Wittman, M. D. Stud. Nat. Prod. Chem. 1989, 3, 233. (e) Ziegler, F. E. Chem. Rev. 1988, 88, 1423. (f) Murray, A. W. Org. React. Mech. 1987, 457; Org. React. Mech. 1986, 429. (g) Moody, C. J. Adv. Heterocycl. Chem. 1987, 42, 203. (h) Barlett, P. A. Tetrahedron 1980, 36, 3. (i) Lutz, R. P. Chem. Rev. 1984, 84, 205. (j) Rhoads, S. J.; Raulins, N. R. Org. React. 1975, 1.
49. Also see: (a) Ito, H.; Taguchi, T. Chem. Soc. Rev. 1999, 28, 43. (b) Enders, D.; Knopp, M.; Schiffers, R. Tetrahedron: Asymmetry 1996, 7, 1847. (c) Blechert, S. Synthesis 1989, 71. (d) Kallmerten, J.; Wittman, M. D. Stud. Nat. Prod. Chem. 1989, 3, 233. (e) Ziegler, F. E. Chem. Rev. 1988, 88, 1423. (f) Murray, A. W. Org. React. Mech. 1987, 457; Org. React. Mech. 1986, 429. (g) Moody, C. J. Adv. Heterocycl. Chem. 1987, 42, 203. (h) Barlett, P. A. Tetrahedron 1980, 36, 3. (i) Lutz, R. P. Chem. Rev. 1984, 84, 205. (j) Rhoads, S. J.; Raulins, N. R. Org. React. 1975, 1.
50. Also see: (a) Ito, H.; Taguchi, T. Chem. Soc. Rev. 1999, 28, 43. (b) Enders, D.; Knopp, M.; Schiffers, R. Tetrahedron: Asymmetry 1996, 7, 1847. (c) Blechert, S. Synthesis 1989, 71. (d) Kallmerten, J.; Wittman, M. D. Stud. Nat. Prod. Chem. 1989, 3, 233. (e) Ziegler, F. E. Chem. Rev. 1988, 88, 1423. (f) Murray, A. W. Org. React. Mech. 1987, 457; Org. React. Mech. 1986, 429. (g) Moody, C. J. Adv. Heterocycl. Chem. 1987, 42, 203. (h) Barlett, P. A. Tetrahedron 1980, 36, 3. (i) Lutz, R. P. Chem. Rev. 1984, 84, 205. (j) Rhoads, S. J.; Raulins, N. R. Org. React. 1975, 1.
51. Also see: (a) Ito, H.; Taguchi, T. Chem. Soc. Rev. 1999, 28, 43. (b) Enders, D.; Knopp, M.; Schiffers, R. Tetrahedron: Asymmetry 1996, 7, 1847. (c) Blechert, S. Synthesis 1989, 71. (d) Kallmerten, J.; Wittman, M. D. Stud. Nat. Prod. Chem. 1989, 3, 233. (e) Ziegler, F. E. Chem. Rev. 1988, 88, 1423. (f) Murray, A. W. Org. React. Mech. 1987, 457; Org. React. Mech. 1986, 429. (g) Moody, C. J. Adv. Heterocycl. Chem. 1987, 42, 203. (h) Barlett, P. A. Tetrahedron 1980, 36, 3. (i) Lutz, R. P. Chem. Rev. 1984, 84, 205. (j) Rhoads, S. J.; Raulins, N. R. Org. React. 1975, 1.
52. Also see: (a) Ito, H.; Taguchi, T. Chem. Soc. Rev. 1999, 28, 43. (b) Enders, D.; Knopp, M.; Schiffers, R. Tetrahedron: Asymmetry 1996, 7, 1847. (c) Blechert, S. Synthesis 1989, 71. (d) Kallmerten, J.; Wittman, M. D. Stud. Nat. Prod. Chem. 1989, 3, 233. (e) Ziegler, F. E. Chem. Rev. 1988, 88, 1423. (f) Murray, A. W. Org. React. Mech. 1987, 457; Org. React. Mech. 1986, 429. (g) Moody, C. J. Adv. Heterocycl. Chem. 1987, 42, 203. (h) Barlett, P. A. Tetrahedron 1980, 36, 3. (i) Lutz, R. P. Chem. Rev. 1984, 84, 205. (j) Rhoads, S. J.; Raulins, N. R. Org. React. 1975, 1.
53. Also see: (a) Ito, H.; Taguchi, T. Chem. Soc. Rev. 1999, 28, 43. (b) Enders, D.; Knopp, M.; Schiffers, R. Tetrahedron: Asymmetry 1996, 7, 1847. (c) Blechert, S. Synthesis 1989, 71. (d) Kallmerten, J.; Wittman, M. D. Stud. Nat. Prod. Chem. 1989, 3, 233. (e) Ziegler, F. E. Chem. Rev. 1988, 88, 1423. (f) Murray, A. W. Org. React. Mech. 1987, 457; Org. React. Mech. 1986, 429. (g) Moody, C. J. Adv. Heterocycl. Chem. 1987, 42, 203. (h) Barlett, P. A. Tetrahedron 1980, 36, 3. (i) Lutz, R. P. Chem. Rev. 1984, 84, 205. (j) Rhoads, S. J.; Raulins, N. R. Org. React. 1975, 1.
54. For some recent elegant studies on stereoselective Claisen rearrangement, see: (a) Hiersemann, M.; Abraham, L. Org. Lett. 2001, 3, 49. (b) Yoon, T. P.; MacMillan, D. W. C. J. Am. Chem. Soc. 2001, 123, 2911. (c) He, S.; Kozmin, S. A.; Rawal, V. H. J. Am. Chem. Soc. 2000, 122, 190. (d) Yoon, T. P.; Dong, V. M. MacMillan, D. W. C. J. Am. Chem. Soc. 1999, 121, 9726. (c) Metz, P.; Hungerhoff, B. J. Org. Chem. 1997, 62, 4442. (d) Welch, J. T.; Eswarakrishnan, S. J. Am. Chem. Soc. 1987, 109, 6716.
55. For some recent elegant studies on stereoselective Claisen rearrangement, see: (a) Hiersemann, M.; Abraham, L. Org. Lett. 2001, 3, 49. (b) Yoon, T. P.; MacMillan, D. W. C. J. Am. Chem. Soc. 2001, 123, 2911. (c) He, S.; Kozmin, S. A.; Rawal, V. H. J. Am. Chem. Soc. 2000, 122, 190. (d) Yoon, T. P.; Dong, V. M. MacMillan, D. W. C. J. Am. Chem. Soc. 1999, 121, 9726. (c) Metz, P.; Hungerhoff, B. J. Org. Chem. 1997, 62, 4442. (d) Welch, J. T.; Eswarakrishnan, S. J. Am. Chem. Soc. 1987, 109, 6716.
56. For some recent elegant studies on stereoselective Claisen rearrangement, see: (a) Hiersemann, M.; Abraham, L. Org. Lett. 2001, 3, 49. (b) Yoon, T. P.; MacMillan, D. W. C. J. Am. Chem. Soc. 2001, 123, 2911. (c) He, S.; Kozmin, S. A.; Rawal, V. H. J. Am. Chem. Soc. 2000, 122, 190. (d) Yoon, T. P.; Dong, V. M. MacMillan, D. W. C. J. Am. Chem. Soc. 1999, 121, 9726. (c) Metz, P.; Hungerhoff, B. J. Org. Chem. 1997, 62, 4442. (d) Welch, J. T.; Eswarakrishnan, S. J. Am. Chem. Soc. 1987, 109, 6716.
57. For some recent elegant studies on stereoselective Claisen rearrangement, see: (a) Hiersemann, M.; Abraham, L. Org. Lett. 2001, 3, 49. (b) Yoon, T. P.; MacMillan, D. W. C. J. Am. Chem. Soc. 2001, 123, 2911. (c) He, S.; Kozmin, S. A.; Rawal, V. H. J. Am. Chem. Soc. 2000, 122, 190. (d) Yoon, T. P.; Dong, V. M. MacMillan, D. W. C. J. Am. Chem. Soc. 1999, 121, 9726. (c) Metz, P.; Hungerhoff, B. J. Org. Chem. 1997, 62, 4442. (d) Welch, J. T.; Eswarakrishnan, S. J. Am. Chem. Soc. 1987, 109, 6716.
58. For some recent elegant studies on stereoselective Claisen rearrangement, see: (a) Hiersemann, M.; Abraham, L. Org. Lett. 2001, 3, 49. (b) Yoon, T. P.; MacMillan, D. W. C. J. Am. Chem. Soc. 2001, 123, 2911. (c) He, S.; Kozmin, S. A.; Rawal, V. H. J. Am. Chem. Soc. 2000, 122, 190. (d) Yoon, T. P.; Dong, V. M. MacMillan, D. W. C. J. Am. Chem. Soc. 1999, 121, 9726. (c) Metz, P.; Hungerhoff, B. J. Org. Chem. 1997, 62, 4442. (d) Welch, J. T.; Eswarakrishnan, S. J. Am. Chem. Soc. 1987, 109, 6716.
59. For some recent elegant studies on stereoselective Claisen rearrangement, see: (a) Hiersemann, M.; Abraham, L. Org. Lett. 2001, 3, 49. (b) Yoon, T. P.; MacMillan, D. W. C. J. Am. Chem. Soc. 2001, 123, 2911. (c) He, S.; Kozmin, S. A.; Rawal, V. H. J. Am. Chem. Soc. 2000, 122, 190. (d) Yoon, T. P.; Dong, V. M. MacMillan, D. W. C. J. Am. Chem. Soc. 1999, 121, 9726. (c) Metz, P.; Hungerhoff, B. J. Org. Chem. 1997, 62, 4442. (d) Welch, J. T.; Eswarakrishnan, S. J. Am. Chem. Soc. 1987, 109, 6716.
60. (a) Ficini, J.; Lumbroso-Bader, N.; Pouliquen, J. Tetrahedron Lett. 1968, 9, 4139.
61. (b) Ficini, J.; Barbara, C. Tetrahedron Lett. 1966, 7, 6425.
62. (c) Nakai, T.; Setoi, H.; Kageyama, Y. Tetrahedron Lett. 1981, 22, 4097.
63. 13C NMR, FTIR, and mass spectroscopy.
64. (a) Sibi, M. P.; Deshpande, P. K.; Ji, J. G. Tetrahedron Lett. 1995, 36, 8965.
65. (b) Sibi, M. P.; Ji, J. G. Angew. Chem., Int. Ed. Engl. 1996, 35, 190.
66. (c) Sibi, M. P.; Porter, N. A. Acc. Chem. Res. 1999, 32, 163.
67. (a) Evans, D. A. Aldrichimica Acta 1982, 15, 23.
68. (b) Heathcock, C. H. Aldrichimica Acta 1990, 23, 99.
69. For a leading reference, see: Hintermann, T.; Seebach, D. Helv. Chim. Acta 1998, 81, 2093.
70. (a) Boeckman, R. K., Jr.; Nelson, S. G.; Gaul, M. D. J. Am. Chem. Soc. 1992, 114, 2258.
71. (b) Boeckman, R. K., Jr.; Boehmler, D. J.; Musselman, R. A. Org. Lett. 2001, 3, 3777.
72. 3 for the enantiomer]. See: Hodgson, D. M.; Foley, A. M.; Boulton, L. T.; Lovell, P. J.; Maw, G. N. J. Chem. Soc., Perkin Trans. 1 1999, 2911.
73. (b) See Supporting Information for characterizations of the E-ketene aminal from 22.
74. Denmark, S. E.; Harmata, M. A. J. Org. Chem. 1983, 48, 3369.
75. (a) Maruoka, K.; Banno, H.; Yamamoto, H. J. Am. Chem. Soc. 1990, 112, 7791.
76. (b) Maruoka, K.; Banno, H.; Yamamoto, H. Tetrahedron: Asymmetry 1991, 2, 647.
77. (c) Maruoka, K.; Yamamoto, H. Synlett 1991, 793.
78. Barlett, P. A.; Hahne, W. F. J. Org. Chem. 1979, 44, 882.
79. Evans, D. A.; Britton, T. C.; Ellman, J. A. Tetrahedron Lett. 1987, 49, 6141.
80. (a) Bartlett, P. A.; Myerson, J. J. Am. Chem. Soc. 1978, 100, 3950.
81. (b) Bartlett, P. A.; Pizzo, C. F. J. Org. Chem. 1981, 46, 3896.