First Enantioselective Catalyst for the Rearrangement of Allylic Imidates to Allylic Amides

Journal of Organic Chemistry

Volumn 62, Issue 5, 1997, Pages 1449-1456

  Calter, Michael ^a,b   Hollis, T Keith ^a   Overman, Larry E ^a   Ziller, Joseph ^a   Zipp, G Greg ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b VIRGINIA POLYTECHNIC INSTITUTE AND STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000653605     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo962090p     Document Type: Article

References (59)

1. (a) Overman, L. E. J. Am. Chem. Soc. 1974, 96, 597.
2. (b) Overman, L. E. J. Am. Chem. Soc. 1976, 98, 2901.
3. (c) Overman, L. E. Acc. Chem. Res. 1980, 13, 218.
4. Representative examples include: (a) Vyas, D. M.; Chiang, Y.; Doyle, T. W. J. Org. Chem. 1984, 49, 2037. (b) Hauser, F. M.; Ellenberger, S. R.; Glusker, J. P.; Smart, C. J.; Carrell, H. L. J. Org. Chem. 1986, 51, 50. (c) Roush, W. R.; Straub, J. A.; Brown, R. J. J. Org. Chem. 1987, 52, 5127. (d) Grigg, R.; Santhakumar, V.; Sridharan, V.; Thornton-Pett, M.; Bridge, A. W. Tetrahedron 1993, 49, 5177. (e) Danishefsky, S.; Lee, J. Y. J. Am. Chem. Soc. 1989, 111, 4829. (f) Saksena, A. K; Lovey, R. G.: Girijavallabhan, V. M.; Ganguly, A. K.; McPhail, A. T. J. Org. Chem. 1986, 51, 5024. (g) Isobe, M.; Fukuda, Y.; Nishikawa, T.; Chabert, P.; Kawai, T.; Goto, T. Tetrahedron Lett. 1990, 37, 3327. (h) Flynn, D. L.; Becker, D. P.; Nosal, R.; Zabrowski, D. L. Tetrahedron Lett. 1992, 33, 7283. (i) Takano, S.; Akiyama, M.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1984, 770. (j) Mehmandoust, ML; Petit, Y.; Larchevêque, M. Tetrahedron Lett. 1992, 33, 4313. (k) Doherty, A. M.; Kornberg, B. E.; Reily, M. D. J. Org. Chem. 1993, 58, 795. (1) Gonda, J.; Helland, A.-C.; Ernst, B.; Bellus, D. Synthesis 1993, 729. (m) Chen, A.; Savage, I.; Thomas, E. J.; Wilson, P. D. Tetrahedron Lett. 1993, 34, 6769. (n) Casara, P. Tetrahedron Lett. 1994, 35, 3049.
5. Representative examples include: (a) Vyas, D. M.; Chiang, Y.; Doyle, T. W. J. Org. Chem. 1984, 49, 2037. (b) Hauser, F. M.; Ellenberger, S. R.; Glusker, J. P.; Smart, C. J.; Carrell, H. L. J. Org. Chem. 1986, 51, 50. (c) Roush, W. R.; Straub, J. A.; Brown, R. J. J. Org. Chem. 1987, 52, 5127. (d) Grigg, R.; Santhakumar, V.; Sridharan, V.; Thornton-Pett, M.; Bridge, A. W. Tetrahedron 1993, 49, 5177. (e) Danishefsky, S.; Lee, J. Y. J. Am. Chem. Soc. 1989, 111, 4829. (f) Saksena, A. K; Lovey, R. G.: Girijavallabhan, V. M.; Ganguly, A. K.; McPhail, A. T. J. Org. Chem. 1986, 51, 5024. (g) Isobe, M.; Fukuda, Y.; Nishikawa, T.; Chabert, P.; Kawai, T.; Goto, T. Tetrahedron Lett. 1990, 37, 3327. (h) Flynn, D. L.; Becker, D. P.; Nosal, R.; Zabrowski, D. L. Tetrahedron Lett. 1992, 33, 7283. (i) Takano, S.; Akiyama, M.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1984, 770. (j) Mehmandoust, ML; Petit, Y.; Larchevêque, M. Tetrahedron Lett. 1992, 33, 4313. (k) Doherty, A. M.; Kornberg, B. E.; Reily, M. D. J. Org. Chem. 1993, 58, 795. (1) Gonda, J.; Helland, A.-C.; Ernst, B.; Bellus, D. Synthesis 1993, 729. (m) Chen, A.; Savage, I.; Thomas, E. J.; Wilson, P. D. Tetrahedron Lett. 1993, 34, 6769. (n) Casara, P. Tetrahedron Lett. 1994, 35, 3049.
6. Representative examples include: (a) Vyas, D. M.; Chiang, Y.; Doyle, T. W. J. Org. Chem. 1984, 49, 2037. (b) Hauser, F. M.; Ellenberger, S. R.; Glusker, J. P.; Smart, C. J.; Carrell, H. L. J. Org. Chem. 1986, 51, 50. (c) Roush, W. R.; Straub, J. A.; Brown, R. J. J. Org. Chem. 1987, 52, 5127. (d) Grigg, R.; Santhakumar, V.; Sridharan, V.; Thornton-Pett, M.; Bridge, A. W. Tetrahedron 1993, 49, 5177. (e) Danishefsky, S.; Lee, J. Y. J. Am. Chem. Soc. 1989, 111, 4829. (f) Saksena, A. K; Lovey, R. G.: Girijavallabhan, V. M.; Ganguly, A. K.; McPhail, A. T. J. Org. Chem. 1986, 51, 5024. (g) Isobe, M.; Fukuda, Y.; Nishikawa, T.; Chabert, P.; Kawai, T.; Goto, T. Tetrahedron Lett. 1990, 37, 3327. (h) Flynn, D. L.; Becker, D. P.; Nosal, R.; Zabrowski, D. L. Tetrahedron Lett. 1992, 33, 7283. (i) Takano, S.; Akiyama, M.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1984, 770. (j) Mehmandoust, ML; Petit, Y.; Larchevêque, M. Tetrahedron Lett. 1992, 33, 4313. (k) Doherty, A. M.; Kornberg, B. E.; Reily, M. D. J. Org. Chem. 1993, 58, 795. (1) Gonda, J.; Helland, A.-C.; Ernst, B.; Bellus, D. Synthesis 1993, 729. (m) Chen, A.; Savage, I.; Thomas, E. J.; Wilson, P. D. Tetrahedron Lett. 1993, 34, 6769. (n) Casara, P. Tetrahedron Lett. 1994, 35, 3049.
7. Representative examples include: (a) Vyas, D. M.; Chiang, Y.; Doyle, T. W. J. Org. Chem. 1984, 49, 2037. (b) Hauser, F. M.; Ellenberger, S. R.; Glusker, J. P.; Smart, C. J.; Carrell, H. L. J. Org. Chem. 1986, 51, 50. (c) Roush, W. R.; Straub, J. A.; Brown, R. J. J. Org. Chem. 1987, 52, 5127. (d) Grigg, R.; Santhakumar, V.; Sridharan, V.; Thornton-Pett, M.; Bridge, A. W. Tetrahedron 1993, 49, 5177. (e) Danishefsky, S.; Lee, J. Y. J. Am. Chem. Soc. 1989, 111, 4829. (f) Saksena, A. K; Lovey, R. G.: Girijavallabhan, V. M.; Ganguly, A. K.; McPhail, A. T. J. Org. Chem. 1986, 51, 5024. (g) Isobe, M.; Fukuda, Y.; Nishikawa, T.; Chabert, P.; Kawai, T.; Goto, T. Tetrahedron Lett. 1990, 37, 3327. (h) Flynn, D. L.; Becker, D. P.; Nosal, R.; Zabrowski, D. L. Tetrahedron Lett. 1992, 33, 7283. (i) Takano, S.; Akiyama, M.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1984, 770. (j) Mehmandoust, ML; Petit, Y.; Larchevêque, M. Tetrahedron Lett. 1992, 33, 4313. (k) Doherty, A. M.; Kornberg, B. E.; Reily, M. D. J. Org. Chem. 1993, 58, 795. (1) Gonda, J.; Helland, A.-C.; Ernst, B.; Bellus, D. Synthesis 1993, 729. (m) Chen, A.; Savage, I.; Thomas, E. J.; Wilson, P. D. Tetrahedron Lett. 1993, 34, 6769. (n) Casara, P. Tetrahedron Lett. 1994, 35, 3049.
8. Representative examples include: (a) Vyas, D. M.; Chiang, Y.; Doyle, T. W. J. Org. Chem. 1984, 49, 2037. (b) Hauser, F. M.; Ellenberger, S. R.; Glusker, J. P.; Smart, C. J.; Carrell, H. L. J. Org. Chem. 1986, 51, 50. (c) Roush, W. R.; Straub, J. A.; Brown, R. J. J. Org. Chem. 1987, 52, 5127. (d) Grigg, R.; Santhakumar, V.; Sridharan, V.; Thornton-Pett, M.; Bridge, A. W. Tetrahedron 1993, 49, 5177. (e) Danishefsky, S.; Lee, J. Y. J. Am. Chem. Soc. 1989, 111, 4829. (f) Saksena, A. K; Lovey, R. G.: Girijavallabhan, V. M.; Ganguly, A. K.; McPhail, A. T. J. Org. Chem. 1986, 51, 5024. (g) Isobe, M.; Fukuda, Y.; Nishikawa, T.; Chabert, P.; Kawai, T.; Goto, T. Tetrahedron Lett. 1990, 37, 3327. (h) Flynn, D. L.; Becker, D. P.; Nosal, R.; Zabrowski, D. L. Tetrahedron Lett. 1992, 33, 7283. (i) Takano, S.; Akiyama, M.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1984, 770. (j) Mehmandoust, ML; Petit, Y.; Larchevêque, M. Tetrahedron Lett. 1992, 33, 4313. (k) Doherty, A. M.; Kornberg, B. E.; Reily, M. D. J. Org. Chem. 1993, 58, 795. (1) Gonda, J.; Helland, A.-C.; Ernst, B.; Bellus, D. Synthesis 1993, 729. (m) Chen, A.; Savage, I.; Thomas, E. J.; Wilson, P. D. Tetrahedron Lett. 1993, 34, 6769. (n) Casara, P. Tetrahedron Lett. 1994, 35, 3049.
9. Representative examples include: (a) Vyas, D. M.; Chiang, Y.; Doyle, T. W. J. Org. Chem. 1984, 49, 2037. (b) Hauser, F. M.; Ellenberger, S. R.; Glusker, J. P.; Smart, C. J.; Carrell, H. L. J. Org. Chem. 1986, 51, 50. (c) Roush, W. R.; Straub, J. A.; Brown, R. J. J. Org. Chem. 1987, 52, 5127. (d) Grigg, R.; Santhakumar, V.; Sridharan, V.; Thornton-Pett, M.; Bridge, A. W. Tetrahedron 1993, 49, 5177. (e) Danishefsky, S.; Lee, J. Y. J. Am. Chem. Soc. 1989, 111, 4829. (f) Saksena, A. K; Lovey, R. G.: Girijavallabhan, V. M.; Ganguly, A. K.; McPhail, A. T. J. Org. Chem. 1986, 51, 5024. (g) Isobe, M.; Fukuda, Y.; Nishikawa, T.; Chabert, P.; Kawai, T.; Goto, T. Tetrahedron Lett. 1990, 37, 3327. (h) Flynn, D. L.; Becker, D. P.; Nosal, R.; Zabrowski, D. L. Tetrahedron Lett. 1992, 33, 7283. (i) Takano, S.; Akiyama, M.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1984, 770. (j) Mehmandoust, ML; Petit, Y.; Larchevêque, M. Tetrahedron Lett. 1992, 33, 4313. (k) Doherty, A. M.; Kornberg, B. E.; Reily, M. D. J. Org. Chem. 1993, 58, 795. (1) Gonda, J.; Helland, A.-C.; Ernst, B.; Bellus, D. Synthesis 1993, 729. (m) Chen, A.; Savage, I.; Thomas, E. J.; Wilson, P. D. Tetrahedron Lett. 1993, 34, 6769. (n) Casara, P. Tetrahedron Lett. 1994, 35, 3049.
10. Representative examples include: (a) Vyas, D. M.; Chiang, Y.; Doyle, T. W. J. Org. Chem. 1984, 49, 2037. (b) Hauser, F. M.; Ellenberger, S. R.; Glusker, J. P.; Smart, C. J.; Carrell, H. L. J. Org. Chem. 1986, 51, 50. (c) Roush, W. R.; Straub, J. A.; Brown, R. J. J. Org. Chem. 1987, 52, 5127. (d) Grigg, R.; Santhakumar, V.; Sridharan, V.; Thornton-Pett, M.; Bridge, A. W. Tetrahedron 1993, 49, 5177. (e) Danishefsky, S.; Lee, J. Y. J. Am. Chem. Soc. 1989, 111, 4829. (f) Saksena, A. K; Lovey, R. G.: Girijavallabhan, V. M.; Ganguly, A. K.; McPhail, A. T. J. Org. Chem. 1986, 51, 5024. (g) Isobe, M.; Fukuda, Y.; Nishikawa, T.; Chabert, P.; Kawai, T.; Goto, T. Tetrahedron Lett. 1990, 37, 3327. (h) Flynn, D. L.; Becker, D. P.; Nosal, R.; Zabrowski, D. L. Tetrahedron Lett. 1992, 33, 7283. (i) Takano, S.; Akiyama, M.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1984, 770. (j) Mehmandoust, ML; Petit, Y.; Larchevêque, M. Tetrahedron Lett. 1992, 33, 4313. (k) Doherty, A. M.; Kornberg, B. E.; Reily, M. D. J. Org. Chem. 1993, 58, 795. (1) Gonda, J.; Helland, A.-C.; Ernst, B.; Bellus, D. Synthesis 1993, 729. (m) Chen, A.; Savage, I.; Thomas, E. J.; Wilson, P. D. Tetrahedron Lett. 1993, 34, 6769. (n) Casara, P. Tetrahedron Lett. 1994, 35, 3049.
11. Representative examples include: (a) Vyas, D. M.; Chiang, Y.; Doyle, T. W. J. Org. Chem. 1984, 49, 2037. (b) Hauser, F. M.; Ellenberger, S. R.; Glusker, J. P.; Smart, C. J.; Carrell, H. L. J. Org. Chem. 1986, 51, 50. (c) Roush, W. R.; Straub, J. A.; Brown, R. J. J. Org. Chem. 1987, 52, 5127. (d) Grigg, R.; Santhakumar, V.; Sridharan, V.; Thornton-Pett, M.; Bridge, A. W. Tetrahedron 1993, 49, 5177. (e) Danishefsky, S.; Lee, J. Y. J. Am. Chem. Soc. 1989, 111, 4829. (f) Saksena, A. K; Lovey, R. G.: Girijavallabhan, V. M.; Ganguly, A. K.; McPhail, A. T. J. Org. Chem. 1986, 51, 5024. (g) Isobe, M.; Fukuda, Y.; Nishikawa, T.; Chabert, P.; Kawai, T.; Goto, T. Tetrahedron Lett. 1990, 37, 3327. (h) Flynn, D. L.; Becker, D. P.; Nosal, R.; Zabrowski, D. L. Tetrahedron Lett. 1992, 33, 7283. (i) Takano, S.; Akiyama, M.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1984, 770. (j) Mehmandoust, ML; Petit, Y.; Larchevêque, M. Tetrahedron Lett. 1992, 33, 4313. (k) Doherty, A. M.; Kornberg, B. E.; Reily, M. D. J. Org. Chem. 1993, 58, 795. (1) Gonda, J.; Helland, A.-C.; Ernst, B.; Bellus, D. Synthesis 1993, 729. (m) Chen, A.; Savage, I.; Thomas, E. J.; Wilson, P. D. Tetrahedron Lett. 1993, 34, 6769. (n) Casara, P. Tetrahedron Lett. 1994, 35, 3049.
12. Representative examples include: (a) Vyas, D. M.; Chiang, Y.; Doyle, T. W. J. Org. Chem. 1984, 49, 2037. (b) Hauser, F. M.; Ellenberger, S. R.; Glusker, J. P.; Smart, C. J.; Carrell, H. L. J. Org. Chem. 1986, 51, 50. (c) Roush, W. R.; Straub, J. A.; Brown, R. J. J. Org. Chem. 1987, 52, 5127. (d) Grigg, R.; Santhakumar, V.; Sridharan, V.; Thornton-Pett, M.; Bridge, A. W. Tetrahedron 1993, 49, 5177. (e) Danishefsky, S.; Lee, J. Y. J. Am. Chem. Soc. 1989, 111, 4829. (f) Saksena, A. K; Lovey, R. G.: Girijavallabhan, V. M.; Ganguly, A. K.; McPhail, A. T. J. Org. Chem. 1986, 51, 5024. (g) Isobe, M.; Fukuda, Y.; Nishikawa, T.; Chabert, P.; Kawai, T.; Goto, T. Tetrahedron Lett. 1990, 37, 3327. (h) Flynn, D. L.; Becker, D. P.; Nosal, R.; Zabrowski, D. L. Tetrahedron Lett. 1992, 33, 7283. (i) Takano, S.; Akiyama, M.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1984, 770. (j) Mehmandoust, ML; Petit, Y.; Larchevêque, M. Tetrahedron Lett. 1992, 33, 4313. (k) Doherty, A. M.; Kornberg, B. E.; Reily, M. D. J. Org. Chem. 1993, 58, 795. (1) Gonda, J.; Helland, A.-C.; Ernst, B.; Bellus, D. Synthesis 1993, 729. (m) Chen, A.; Savage, I.; Thomas, E. J.; Wilson, P. D. Tetrahedron Lett. 1993, 34, 6769. (n) Casara, P. Tetrahedron Lett. 1994, 35, 3049.
13. Representative examples include: (a) Vyas, D. M.; Chiang, Y.; Doyle, T. W. J. Org. Chem. 1984, 49, 2037. (b) Hauser, F. M.; Ellenberger, S. R.; Glusker, J. P.; Smart, C. J.; Carrell, H. L. J. Org. Chem. 1986, 51, 50. (c) Roush, W. R.; Straub, J. A.; Brown, R. J. J. Org. Chem. 1987, 52, 5127. (d) Grigg, R.; Santhakumar, V.; Sridharan, V.; Thornton-Pett, M.; Bridge, A. W. Tetrahedron 1993, 49, 5177. (e) Danishefsky, S.; Lee, J. Y. J. Am. Chem. Soc. 1989, 111, 4829. (f) Saksena, A. K; Lovey, R. G.: Girijavallabhan, V. M.; Ganguly, A. K.; McPhail, A. T. J. Org. Chem. 1986, 51, 5024. (g) Isobe, M.; Fukuda, Y.; Nishikawa, T.; Chabert, P.; Kawai, T.; Goto, T. Tetrahedron Lett. 1990, 37, 3327. (h) Flynn, D. L.; Becker, D. P.; Nosal, R.; Zabrowski, D. L. Tetrahedron Lett. 1992, 33, 7283. (i) Takano, S.; Akiyama, M.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1984, 770. (j) Mehmandoust, ML; Petit, Y.; Larchevêque, M. Tetrahedron Lett. 1992, 33, 4313. (k) Doherty, A. M.; Kornberg, B. E.; Reily, M. D. J. Org. Chem. 1993, 58, 795. (1) Gonda, J.; Helland, A.-C.; Ernst, B.; Bellus, D. Synthesis 1993, 729. (m) Chen, A.; Savage, I.; Thomas, E. J.; Wilson, P. D. Tetrahedron Lett. 1993, 34, 6769. (n) Casara, P. Tetrahedron Lett. 1994, 35, 3049.
14. Representative examples include: (a) Vyas, D. M.; Chiang, Y.; Doyle, T. W. J. Org. Chem. 1984, 49, 2037. (b) Hauser, F. M.; Ellenberger, S. R.; Glusker, J. P.; Smart, C. J.; Carrell, H. L. J. Org. Chem. 1986, 51, 50. (c) Roush, W. R.; Straub, J. A.; Brown, R. J. J. Org. Chem. 1987, 52, 5127. (d) Grigg, R.; Santhakumar, V.; Sridharan, V.; Thornton-Pett, M.; Bridge, A. W. Tetrahedron 1993, 49, 5177. (e) Danishefsky, S.; Lee, J. Y. J. Am. Chem. Soc. 1989, 111, 4829. (f) Saksena, A. K; Lovey, R. G.: Girijavallabhan, V. M.; Ganguly, A. K.; McPhail, A. T. J. Org. Chem. 1986, 51, 5024. (g) Isobe, M.; Fukuda, Y.; Nishikawa, T.; Chabert, P.; Kawai, T.; Goto, T. Tetrahedron Lett. 1990, 37, 3327. (h) Flynn, D. L.; Becker, D. P.; Nosal, R.; Zabrowski, D. L. Tetrahedron Lett. 1992, 33, 7283. (i) Takano, S.; Akiyama, M.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1984, 770. (j) Mehmandoust, ML; Petit, Y.; Larchevêque, M. Tetrahedron Lett. 1992, 33, 4313. (k) Doherty, A. M.; Kornberg, B. E.; Reily, M. D. J. Org. Chem. 1993, 58, 795. (1) Gonda, J.; Helland, A.-C.; Ernst, B.; Bellus, D. Synthesis 1993, 729. (m) Chen, A.; Savage, I.; Thomas, E. J.; Wilson, P. D. Tetrahedron Lett. 1993, 34, 6769. (n) Casara, P. Tetrahedron Lett. 1994, 35, 3049.
15. Representative examples include: (a) Vyas, D. M.; Chiang, Y.; Doyle, T. W. J. Org. Chem. 1984, 49, 2037. (b) Hauser, F. M.; Ellenberger, S. R.; Glusker, J. P.; Smart, C. J.; Carrell, H. L. J. Org. Chem. 1986, 51, 50. (c) Roush, W. R.; Straub, J. A.; Brown, R. J. J. Org. Chem. 1987, 52, 5127. (d) Grigg, R.; Santhakumar, V.; Sridharan, V.; Thornton-Pett, M.; Bridge, A. W. Tetrahedron 1993, 49, 5177. (e) Danishefsky, S.; Lee, J. Y. J. Am. Chem. Soc. 1989, 111, 4829. (f) Saksena, A. K; Lovey, R. G.: Girijavallabhan, V. M.; Ganguly, A. K.; McPhail, A. T. J. Org. Chem. 1986, 51, 5024. (g) Isobe, M.; Fukuda, Y.; Nishikawa, T.; Chabert, P.; Kawai, T.; Goto, T. Tetrahedron Lett. 1990, 37, 3327. (h) Flynn, D. L.; Becker, D. P.; Nosal, R.; Zabrowski, D. L. Tetrahedron Lett. 1992, 33, 7283. (i) Takano, S.; Akiyama, M.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1984, 770. (j) Mehmandoust, ML; Petit, Y.; Larchevêque, M. Tetrahedron Lett. 1992, 33, 4313. (k) Doherty, A. M.; Kornberg, B. E.; Reily, M. D. J. Org. Chem. 1993, 58, 795. (1) Gonda, J.; Helland, A.-C.; Ernst, B.; Bellus, D. Synthesis 1993, 729. (m) Chen, A.; Savage, I.; Thomas, E. J.; Wilson, P. D. Tetrahedron Lett. 1993, 34, 6769. (n) Casara, P. Tetrahedron Lett. 1994, 35, 3049.
16. Representative examples include: (a) Vyas, D. M.; Chiang, Y.; Doyle, T. W. J. Org. Chem. 1984, 49, 2037. (b) Hauser, F. M.; Ellenberger, S. R.; Glusker, J. P.; Smart, C. J.; Carrell, H. L. J. Org. Chem. 1986, 51, 50. (c) Roush, W. R.; Straub, J. A.; Brown, R. J. J. Org. Chem. 1987, 52, 5127. (d) Grigg, R.; Santhakumar, V.; Sridharan, V.; Thornton-Pett, M.; Bridge, A. W. Tetrahedron 1993, 49, 5177. (e) Danishefsky, S.; Lee, J. Y. J. Am. Chem. Soc. 1989, 111, 4829. (f) Saksena, A. K; Lovey, R. G.: Girijavallabhan, V. M.; Ganguly, A. K.; McPhail, A. T. J. Org. Chem. 1986, 51, 5024. (g) Isobe, M.; Fukuda, Y.; Nishikawa, T.; Chabert, P.; Kawai, T.; Goto, T. Tetrahedron Lett. 1990, 37, 3327. (h) Flynn, D. L.; Becker, D. P.; Nosal, R.; Zabrowski, D. L. Tetrahedron Lett. 1992, 33, 7283. (i) Takano, S.; Akiyama, M.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1984, 770. (j) Mehmandoust, ML; Petit, Y.; Larchevêque, M. Tetrahedron Lett. 1992, 33, 4313. (k) Doherty, A. M.; Kornberg, B. E.; Reily, M. D. J. Org. Chem. 1993, 58, 795. (1) Gonda, J.; Helland, A.-C.; Ernst, B.; Bellus, D. Synthesis 1993, 729. (m) Chen, A.; Savage, I.; Thomas, E. J.; Wilson, P. D. Tetrahedron Lett. 1993, 34, 6769. (n) Casara, P. Tetrahedron Lett. 1994, 35, 3049.
17. Representative examples include: (a) Vyas, D. M.; Chiang, Y.; Doyle, T. W. J. Org. Chem. 1984, 49, 2037. (b) Hauser, F. M.; Ellenberger, S. R.; Glusker, J. P.; Smart, C. J.; Carrell, H. L. J. Org. Chem. 1986, 51, 50. (c) Roush, W. R.; Straub, J. A.; Brown, R. J. J. Org. Chem. 1987, 52, 5127. (d) Grigg, R.; Santhakumar, V.; Sridharan, V.; Thornton-Pett, M.; Bridge, A. W. Tetrahedron 1993, 49, 5177. (e) Danishefsky, S.; Lee, J. Y. J. Am. Chem. Soc. 1989, 111, 4829. (f) Saksena, A. K; Lovey, R. G.: Girijavallabhan, V. M.; Ganguly, A. K.; McPhail, A. T. J. Org. Chem. 1986, 51, 5024. (g) Isobe, M.; Fukuda, Y.; Nishikawa, T.; Chabert, P.; Kawai, T.; Goto, T. Tetrahedron Lett. 1990, 37, 3327. (h) Flynn, D. L.; Becker, D. P.; Nosal, R.; Zabrowski, D. L. Tetrahedron Lett. 1992, 33, 7283. (i) Takano, S.; Akiyama, M.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1984, 770. (j) Mehmandoust, ML; Petit, Y.; Larchevêque, M. Tetrahedron Lett. 1992, 33, 4313. (k) Doherty, A. M.; Kornberg, B. E.; Reily, M. D. J. Org. Chem. 1993, 58, 795. (1) Gonda, J.; Helland, A.-C.; Ernst, B.; Bellus, D. Synthesis 1993, 729. (m) Chen, A.; Savage, I.; Thomas, E. J.; Wilson, P. D. Tetrahedron Lett. 1993, 34, 6769. (n) Casara, P. Tetrahedron Lett. 1994, 35, 3049.
18. (a) Ikariya, T.; Ishikawa, Y.; Hirai, K.; Yoshikawa, S. Chem. Lett. 1982, 1815.
19. (b) Metz, P.; Mues, C.; Schoop, A. Tetrahedron 1992, 48, 1071.
20. (c) Mehmandoust, M.; Petit, Y.; Larchevêque, M. Tetrahedron Lett. 1992, 33, 4313.
21. (d) Gonda, J.; Helland, A.-C.; Ernst, B.; Bellus, D. Synthesis 1993, 729.
22. Overman. L. E. Angew. Chem., Int. Ed. Engl. 1984, 23, 579.
23. Schenck, T. G.; Bosnich, B. J. Am. Chem. Soc. 1985, 107, 2058.
24. In a catalytic asymmetric reaction, the first irreversible enantiodifferentiating step determines asymmetric induction, see: Landis, C. R.; Halpern, J. J. Am. Chem. Soc. 1987, 109, 1746. For an exception, see: Zhang, W.; Lee, N. H.; Jacobsen, E. N. J. Am. Chem. Soc. 1994, 116, 425.
25. In a catalytic asymmetric reaction, the first irreversible enantiodifferentiating step determines asymmetric induction, see: Landis, C. R.; Halpern, J. J. Am. Chem. Soc. 1987, 109, 1746. For an exception, see: Zhang, W.; Lee, N. H.; Jacobsen, E. N. J. Am. Chem. Soc. 1994, 116, 425.
26. 2
27. Yamamoto, Y.; Shimoda, H.; Oda, J.; Inouye, Y. Bull. Chem. Soc. Jpn. 1976, 49, 3247.
28. 2 promoted elimination of allylic imidates. Unpublished studies of A. Renaldo, UCI, 1983.
29. 2].
30. Annibale, G.; Cattalini, L.; Bertolasi, V.; Ferreti, V.; Gilli, G.; Tobe, M. L. J. Chem. Soc., Dalton Trans. 1989, 1265.
31. These experiments are summarized in the Supporting Information. For a recent review of oxazolidine-derived asymmetric catalysts, see: Ager, O. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835.
32. 4 Lumma, W. C., Jr.; Wohl, R. A.; Davey, D. D.; Argentieri, T. M.; DeVita, R. J.; Gomez, R. P.; Jain, V. K.; Marisca, A. J.; Morgan, T. K., Jr.; Reiser, H. J.; Sullivan, M. E.; Wiggins, J.; Wong, S. S. J. Med. Chem. 1987, 30, 755.
33. (a) Dokuzovic, Z., Roberts, N. K, Sawyer, J. F., Whelan, J., Bosnich, B. J. Am. Chem. Soc. 1986, 108, 2034.
34. (b) Mukaiyama, T.; Asami. M. Top. Curr. Chem. 1985, 127, 133.
35. Brookhart, M.; Green, M. L. H. J. Organomet. Chem. 1983, 250, 395. Crabtree, R. H.; Hamilton, D. G. Adv. Organomet. Chem. 1988, 28, 299.
36. Brookhart, M.; Green, M. L. H. J. Organomet. Chem. 1983, 250, 395. Crabtree, R. H.; Hamilton, D. G. Adv. Organomet. Chem. 1988, 28, 299.
37. For other applications of this ligand, see, inter alia, Kobayashi, S.; Horibe, M. J. Am. Chem. Soc. 1994, 116, 9805.
38. A search of the Cambridge Crystallographic Data base revealed only one simple diamine that bridged two palladium atoms. This example involved a trans-2,3-norbornyldiamine that cannot form the simple chelate. Hatano, K.; Saito, R. Bull. Chem. Soc. Jpn. 1993, 66, 3818.
39. Crystallographic data has been deposited with the Cambridge Crystallographic Data Centre. The coordinates can be obtained on request from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.
40. Orpen, A. G.; Brammer, L.; Allen, F. H.; Kennard, O.; Watson, D. G.; Taylor, R. J. Chem. Soc., Dalton Trans. 1989, S1.
41. Albeniz, A. C.; Espinet, P. In Encyclopedia of Inorganic Chemistry; King, R. B., Ed.; John Wiley & Sons: New York, 1994; Vol. 6, p 3010.
42. Meek, D. W.; Nicpon P. E.; Meek, V. I. J. Am. Chem. Soc. 1970, 92, 5351.
43. 4 to Pd(II) has been described, see: (a) Crociani, B.; Di Bianca, F., Canovese, L.; Uguagliati, P. J. Organomet. Chem. 1990, 381, C17. (b) Garrou, P. E. Chem. Rev. 1985, 85, 171.
44. 4 to Pd(II) has been described, see: (a) Crociani, B.; Di Bianca, F., Canovese, L.; Uguagliati, P. J. Organomet. Chem. 1990, 381, C17. (b) Garrou, P. E. Chem. Rev. 1985, 85, 171.
45. Overman, L. E.; Zipp, G. G. J. Org. Chem. 1997, 62, in press.
46. 24 (22% ee by HPLC analysis using a Chiracel OD column) was isolated in 30% yield from rearrangement of 32 with 18.
47. 2 were also examined. The rearranged amides iii (37% ee by HPLC analysis using a Chiracel OD column) and iv (42% ee by HPLC analysis using a Chiracel AS column) were obtained in low yield and shown by chemical correlation to have the same absolute configuration as (-)-30. Chemical equation presented.
48. 2, 40°C, 48 h) to produce (+)-30 in 86% yield and 63% ee. The rearrangement of other imidates has not been examined with catalyst 23, since our current efforts focus on a more promising catalyst type (K. Hollis, unpublished results).
49. Several achiral and chiral sulfoxides were used to modify the coordination sphere of 18 in an unsuccessful attempt to improve enantioselection in the rearrangement of allylic imidate 29. Details are provided in the Supporting Information.
50. Dickman, D. A.; Meyers, A. I.; Smith, G. A.; Gawley, R. E. Organic Syntheses; Wiley, New York, 1990; Collect. Vol, VII, p 530. Rinaldi, P. L.; Wilk, M. J. J. Org. Chem. 1986, 48, 2141.
51. Dickman, D. A.; Meyers, A. I.; Smith, G. A.; Gawley, R. E. Organic Syntheses; Wiley, New York, 1990; Collect. Vol, VII, p 530. Rinaldi, P. L.; Wilk, M. J. J. Org. Chem. 1986, 48, 2141.
52. Wolfe, J. P.; Wagaw, S.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 7215.
53. Callahan, F. M.; Anderson, G. W.; Paul, R.; Zimmerman, J. E. J. Am. Chem. Soc. 1963, 85, 201.
54. 2 under nitrogen. High resolution mass spectra were measured on a MicroMass Analytical 7070E (EI or CI-isobutane); uncertainty (σ) in mass measurments is 1.0 millimass unit (molecular weight < 400) or 1.5 millimass units (molecular weight 400-1000). Other general experimental details have been detailed: Deng, W.; Overman, L. E. J. Am. Chem. Soc. 1994, 116, 11241.
55. 2 under nitrogen. High resolution mass spectra were measured on a MicroMass Analytical 7070E (EI or CI-isobutane); uncertainty (σ) in mass measurments is 1.0 millimass unit (molecular weight < 400) or 1.5 millimass units (molecular weight 400-1000). Other general experimental details have been detailed: Deng, W.; Overman, L. E. J. Am. Chem. Soc. 1994, 116, 11241.
56. A racemic sample was prepared from racemic proline and analyzed on a Chiracel OD HPLC column (5% i-PrOH/hexane) giving two peaks; the diamine prepared from (S)-proline showed only a single peak.
57. 35
58. Arana, C. R.; Abruna, H. D. Inorg. Chem. 1993, 32, 194.
59. NMR spectra of this material are broad and complex; representative examples are provided in the Supporting Information.