Tandem 5 + 2/3 + 2 and 5 + 2/3 + 3 Cycloaddition Reactions

Journal of Organic Chemistry

Volumn 62, Issue 24, 1997, Pages 8274-8275

  Engler, Thomas A ^a   Scheibe, Cynthia M ^a   Iyengar, Rajesh ^a  

^a UNIVERSITY OF KANSAS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000960728     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971601k     Document Type: Article

References (53)

1. For reviews and summaries of various processes, see (a) Ho, T.-L. Tandem Organic Reactions; Wiley-Interscience: New York; 1992. (b) Ho, T.-L. Tactics of Organic Synthesis; Wiley-Interscience: New York; 1994. Hudlicky, T. Chem. Rev. (Washington, D.C.) 1996, 96, 3-30. Tietze, L. F. Chem. Rev. (Washington, D.C.) 1996, 96, 115-136. (e) Denmark, S. E.; Thorarensen, A. Chem. Rev. (Washington, D.C.) 1996, 96, 137-165. (f) Winkler, J. D. Chem. Rev. (Washington, D.C.) 1996, 96, 167-176. (g) Ryu, I.; Sonoda, N.; Curran, D. P. Chem. Rev. (Washington, D.C.) 1996, 96, 177-194. (h) Parsons, P. J.; Penkett, C. S.; Shell, A. J. Chem. Rev. (Washington, D.C.) 1996, 96, 195-206. Wang, K. K. Chem. Rev. (Washington, D.C.) 1996, 96, 207-222. (j) Padwa, A.; Weingarten, M. D. Chem. Rev. (Washington, D.C.) 1996, 96, 223-269. (k) Harvey, D. F.; Sigano, D. M. Chem. Rev. (Washington, D.C.) 1996, 96, 271-288. Malacria, M. Chem. Rev. (Washington, D.C.) 1996, 96, 289-306. Molander, G. A.; Harris, C. R. Chem. Rev, (Washington, D.C.) 1996, 96, 307-338. (n) Snider, B. B. Chem. Rev. (Washington, D.C.) 1996, 96, 339-363. (o) Negishi, E.-i.; Copéret, C.; Ma, S.; Liou, S.-Y.; Liu, F. Chem. Rev. (Washington, D.C.) 1996, 96, 365-393. (p) Heumann, A.; Réglier, M. Tetrahedron 1996, 52, 9289-9346. (q) Bunce, R. A. Tetrahedron 1995, 51, 13103-13159. (r) Posner, G. H. Chem. Rev. (Washington, D.C.) 1986, 86, 831-844. (s) Skrydstrup, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 345-347.
2. For reviews and summaries of various processes, see (a) Ho, T.-L. Tandem Organic Reactions; Wiley-Interscience: New York; 1992. (b) Ho, T.-L. Tactics of Organic Synthesis; Wiley-Interscience: New York; 1994. Hudlicky, T. Chem. Rev. (Washington, D.C.) 1996, 96, 3-30. Tietze, L. F. Chem. Rev. (Washington, D.C.) 1996, 96, 115-136. (e) Denmark, S. E.; Thorarensen, A. Chem. Rev. (Washington, D.C.) 1996, 96, 137-165. (f) Winkler, J. D. Chem. Rev. (Washington, D.C.) 1996, 96, 167-176. (g) Ryu, I.; Sonoda, N.; Curran, D. P. Chem. Rev. (Washington, D.C.) 1996, 96, 177-194. (h) Parsons, P. J.; Penkett, C. S.; Shell, A. J. Chem. Rev. (Washington, D.C.) 1996, 96, 195-206. Wang, K. K. Chem. Rev. (Washington, D.C.) 1996, 96, 207-222. (j) Padwa, A.; Weingarten, M. D. Chem. Rev. (Washington, D.C.) 1996, 96, 223-269. (k) Harvey, D. F.; Sigano, D. M. Chem. Rev. (Washington, D.C.) 1996, 96, 271-288. Malacria, M. Chem. Rev. (Washington, D.C.) 1996, 96, 289-306. Molander, G. A.; Harris, C. R. Chem. Rev, (Washington, D.C.) 1996, 96, 307-338. (n) Snider, B. B. Chem. Rev. (Washington, D.C.) 1996, 96, 339-363. (o) Negishi, E.-i.; Copéret, C.; Ma, S.; Liou, S.-Y.; Liu, F. Chem. Rev. (Washington, D.C.) 1996, 96, 365-393. (p) Heumann, A.; Réglier, M. Tetrahedron 1996, 52, 9289-9346. (q) Bunce, R. A. Tetrahedron 1995, 51, 13103-13159. (r) Posner, G. H. Chem. Rev. (Washington, D.C.) 1986, 86, 831-844. (s) Skrydstrup, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 345-347.
3. For reviews and summaries of various processes, see (a) Ho, T.-L. Tandem Organic Reactions; Wiley-Interscience: New York; 1992. (b) Ho, T.-L. Tactics of Organic Synthesis; Wiley-Interscience: New York; 1994. Hudlicky, T. Chem. Rev. (Washington, D.C.) 1996, 96, 3-30. Tietze, L. F. Chem. Rev. (Washington, D.C.) 1996, 96, 115-136. (e) Denmark, S. E.; Thorarensen, A. Chem. Rev. (Washington, D.C.) 1996, 96, 137-165. (f) Winkler, J. D. Chem. Rev. (Washington, D.C.) 1996, 96, 167-176. (g) Ryu, I.; Sonoda, N.; Curran, D. P. Chem. Rev. (Washington, D.C.) 1996, 96, 177-194. (h) Parsons, P. J.; Penkett, C. S.; Shell, A. J. Chem. Rev. (Washington, D.C.) 1996, 96, 195-206. Wang, K. K. Chem. Rev. (Washington, D.C.) 1996, 96, 207-222. (j) Padwa, A.; Weingarten, M. D. Chem. Rev. (Washington, D.C.) 1996, 96, 223-269. (k) Harvey, D. F.; Sigano, D. M. Chem. Rev. (Washington, D.C.) 1996, 96, 271-288. Malacria, M. Chem. Rev. (Washington, D.C.) 1996, 96, 289-306. Molander, G. A.; Harris, C. R. Chem. Rev, (Washington, D.C.) 1996, 96, 307-338. (n) Snider, B. B. Chem. Rev. (Washington, D.C.) 1996, 96, 339-363. (o) Negishi, E.-i.; Copéret, C.; Ma, S.; Liou, S.-Y.; Liu, F. Chem. Rev. (Washington, D.C.) 1996, 96, 365-393. (p) Heumann, A.; Réglier, M. Tetrahedron 1996, 52, 9289-9346. (q) Bunce, R. A. Tetrahedron 1995, 51, 13103-13159. (r) Posner, G. H. Chem. Rev. (Washington, D.C.) 1986, 86, 831-844. (s) Skrydstrup, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 345-347.
4. For reviews and summaries of various processes, see (a) Ho, T.-L. Tandem Organic Reactions; Wiley-Interscience: New York; 1992. (b) Ho, T.-L. Tactics of Organic Synthesis; Wiley-Interscience: New York; 1994. Hudlicky, T. Chem. Rev. (Washington, D.C.) 1996, 96, 3-30. Tietze, L. F. Chem. Rev. (Washington, D.C.) 1996, 96, 115-136. (e) Denmark, S. E.; Thorarensen, A. Chem. Rev. (Washington, D.C.) 1996, 96, 137-165. (f) Winkler, J. D. Chem. Rev. (Washington, D.C.) 1996, 96, 167-176. (g) Ryu, I.; Sonoda, N.; Curran, D. P. Chem. Rev. (Washington, D.C.) 1996, 96, 177-194. (h) Parsons, P. J.; Penkett, C. S.; Shell, A. J. Chem. Rev. (Washington, D.C.) 1996, 96, 195-206. Wang, K. K. Chem. Rev. (Washington, D.C.) 1996, 96, 207-222. (j) Padwa, A.; Weingarten, M. D. Chem. Rev. (Washington, D.C.) 1996, 96, 223-269. (k) Harvey, D. F.; Sigano, D. M. Chem. Rev. (Washington, D.C.) 1996, 96, 271-288. Malacria, M. Chem. Rev. (Washington, D.C.) 1996, 96, 289-306. Molander, G. A.; Harris, C. R. Chem. Rev, (Washington, D.C.) 1996, 96, 307-338. (n) Snider, B. B. Chem. Rev. (Washington, D.C.) 1996, 96, 339-363. (o) Negishi, E.-i.; Copéret, C.; Ma, S.; Liou, S.-Y.; Liu, F. Chem. Rev. (Washington, D.C.) 1996, 96, 365-393. (p) Heumann, A.; Réglier, M. Tetrahedron 1996, 52, 9289-9346. (q) Bunce, R. A. Tetrahedron 1995, 51, 13103-13159. (r) Posner, G. H. Chem. Rev. (Washington, D.C.) 1986, 86, 831-844. (s) Skrydstrup, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 345-347.
5. For reviews and summaries of various processes, see (a) Ho, T.-L. Tandem Organic Reactions; Wiley-Interscience: New York; 1992. (b) Ho, T.-L. Tactics of Organic Synthesis; Wiley-Interscience: New York; 1994. Hudlicky, T. Chem. Rev. (Washington, D.C.) 1996, 96, 3-30. Tietze, L. F. Chem. Rev. (Washington, D.C.) 1996, 96, 115-136. (e) Denmark, S. E.; Thorarensen, A. Chem. Rev. (Washington, D.C.) 1996, 96, 137-165. (f) Winkler, J. D. Chem. Rev. (Washington, D.C.) 1996, 96, 167-176. (g) Ryu, I.; Sonoda, N.; Curran, D. P. Chem. Rev. (Washington, D.C.) 1996, 96, 177-194. (h) Parsons, P. J.; Penkett, C. S.; Shell, A. J. Chem. Rev. (Washington, D.C.) 1996, 96, 195-206. Wang, K. K. Chem. Rev. (Washington, D.C.) 1996, 96, 207-222. (j) Padwa, A.; Weingarten, M. D. Chem. Rev. (Washington, D.C.) 1996, 96, 223-269. (k) Harvey, D. F.; Sigano, D. M. Chem. Rev. (Washington, D.C.) 1996, 96, 271-288. Malacria, M. Chem. Rev. (Washington, D.C.) 1996, 96, 289-306. Molander, G. A.; Harris, C. R. Chem. Rev, (Washington, D.C.) 1996, 96, 307-338. (n) Snider, B. B. Chem. Rev. (Washington, D.C.) 1996, 96, 339-363. (o) Negishi, E.-i.; Copéret, C.; Ma, S.; Liou, S.-Y.; Liu, F. Chem. Rev. (Washington, D.C.) 1996, 96, 365-393. (p) Heumann, A.; Réglier, M. Tetrahedron 1996, 52, 9289-9346. (q) Bunce, R. A. Tetrahedron 1995, 51, 13103-13159. (r) Posner, G. H. Chem. Rev. (Washington, D.C.) 1986, 86, 831-844. (s) Skrydstrup, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 345-347.
6. For reviews and summaries of various processes, see (a) Ho, T.-L. Tandem Organic Reactions; Wiley-Interscience: New York; 1992. (b) Ho, T.-L. Tactics of Organic Synthesis; Wiley-Interscience: New York; 1994. Hudlicky, T. Chem. Rev. (Washington, D.C.) 1996, 96, 3-30. Tietze, L. F. Chem. Rev. (Washington, D.C.) 1996, 96, 115-136. (e) Denmark, S. E.; Thorarensen, A. Chem. Rev. (Washington, D.C.) 1996, 96, 137-165. (f) Winkler, J. D. Chem. Rev. (Washington, D.C.) 1996, 96, 167-176. (g) Ryu, I.; Sonoda, N.; Curran, D. P. Chem. Rev. (Washington, D.C.) 1996, 96, 177-194. (h) Parsons, P. J.; Penkett, C. S.; Shell, A. J. Chem. Rev. (Washington, D.C.) 1996, 96, 195-206. Wang, K. K. Chem. Rev. (Washington, D.C.) 1996, 96, 207-222. (j) Padwa, A.; Weingarten, M. D. Chem. Rev. (Washington, D.C.) 1996, 96, 223-269. (k) Harvey, D. F.; Sigano, D. M. Chem. Rev. (Washington, D.C.) 1996, 96, 271-288. Malacria, M. Chem. Rev. (Washington, D.C.) 1996, 96, 289-306. Molander, G. A.; Harris, C. R. Chem. Rev, (Washington, D.C.) 1996, 96, 307-338. (n) Snider, B. B. Chem. Rev. (Washington, D.C.) 1996, 96, 339-363. (o) Negishi, E.-i.; Copéret, C.; Ma, S.; Liou, S.-Y.; Liu, F. Chem. Rev. (Washington, D.C.) 1996, 96, 365-393. (p) Heumann, A.; Réglier, M. Tetrahedron 1996, 52, 9289-9346. (q) Bunce, R. A. Tetrahedron 1995, 51, 13103-13159. (r) Posner, G. H. Chem. Rev. (Washington, D.C.) 1986, 86, 831-844. (s) Skrydstrup, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 345-347.
7. For reviews and summaries of various processes, see (a) Ho, T.-L. Tandem Organic Reactions; Wiley-Interscience: New York; 1992. (b) Ho, T.-L. Tactics of Organic Synthesis; Wiley-Interscience: New York; 1994. Hudlicky, T. Chem. Rev. (Washington, D.C.) 1996, 96, 3-30. Tietze, L. F. Chem. Rev. (Washington, D.C.) 1996, 96, 115-136. (e) Denmark, S. E.; Thorarensen, A. Chem. Rev. (Washington, D.C.) 1996, 96, 137-165. (f) Winkler, J. D. Chem. Rev. (Washington, D.C.) 1996, 96, 167-176. (g) Ryu, I.; Sonoda, N.; Curran, D. P. Chem. Rev. (Washington, D.C.) 1996, 96, 177-194. (h) Parsons, P. J.; Penkett, C. S.; Shell, A. J. Chem. Rev. (Washington, D.C.) 1996, 96, 195-206. Wang, K. K. Chem. Rev. (Washington, D.C.) 1996, 96, 207-222. (j) Padwa, A.; Weingarten, M. D. Chem. Rev. (Washington, D.C.) 1996, 96, 223-269. (k) Harvey, D. F.; Sigano, D. M. Chem. Rev. (Washington, D.C.) 1996, 96, 271-288. Malacria, M. Chem. Rev. (Washington, D.C.) 1996, 96, 289-306. Molander, G. A.; Harris, C. R. Chem. Rev, (Washington, D.C.) 1996, 96, 307-338. (n) Snider, B. B. Chem. Rev. (Washington, D.C.) 1996, 96, 339-363. (o) Negishi, E.-i.; Copéret, C.; Ma, S.; Liou, S.-Y.; Liu, F. Chem. Rev. (Washington, D.C.) 1996, 96, 365-393. (p) Heumann, A.; Réglier, M. Tetrahedron 1996, 52, 9289-9346. (q) Bunce, R. A. Tetrahedron 1995, 51, 13103-13159. (r) Posner, G. H. Chem. Rev. (Washington, D.C.) 1986, 86, 831-844. (s) Skrydstrup, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 345-347.
8. For reviews and summaries of various processes, see (a) Ho, T.-L. Tandem Organic Reactions; Wiley-Interscience: New York; 1992. (b) Ho, T.-L. Tactics of Organic Synthesis; Wiley-Interscience: New York; 1994. Hudlicky, T. Chem. Rev. (Washington, D.C.) 1996, 96, 3-30. Tietze, L. F. Chem. Rev. (Washington, D.C.) 1996, 96, 115-136. (e) Denmark, S. E.; Thorarensen, A. Chem. Rev. (Washington, D.C.) 1996, 96, 137-165. (f) Winkler, J. D. Chem. Rev. (Washington, D.C.) 1996, 96, 167-176. (g) Ryu, I.; Sonoda, N.; Curran, D. P. Chem. Rev. (Washington, D.C.) 1996, 96, 177-194. (h) Parsons, P. J.; Penkett, C. S.; Shell, A. J. Chem. Rev. (Washington, D.C.) 1996, 96, 195-206. Wang, K. K. Chem. Rev. (Washington, D.C.) 1996, 96, 207-222. (j) Padwa, A.; Weingarten, M. D. Chem. Rev. (Washington, D.C.) 1996, 96, 223-269. (k) Harvey, D. F.; Sigano, D. M. Chem. Rev. (Washington, D.C.) 1996, 96, 271-288. Malacria, M. Chem. Rev. (Washington, D.C.) 1996, 96, 289-306. Molander, G. A.; Harris, C. R. Chem. Rev, (Washington, D.C.) 1996, 96, 307-338. (n) Snider, B. B. Chem. Rev. (Washington, D.C.) 1996, 96, 339-363. (o) Negishi, E.-i.; Copéret, C.; Ma, S.; Liou, S.-Y.; Liu, F. Chem. Rev. (Washington, D.C.) 1996, 96, 365-393. (p) Heumann, A.; Réglier, M. Tetrahedron 1996, 52, 9289-9346. (q) Bunce, R. A. Tetrahedron 1995, 51, 13103-13159. (r) Posner, G. H. Chem. Rev. (Washington, D.C.) 1986, 86, 831-844. (s) Skrydstrup, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 345-347.
9. For reviews and summaries of various processes, see (a) Ho, T.-L. Tandem Organic Reactions; Wiley-Interscience: New York; 1992. (b) Ho, T.-L. Tactics of Organic Synthesis; Wiley-Interscience: New York; 1994. Hudlicky, T. Chem. Rev. (Washington, D.C.) 1996, 96, 3-30. Tietze, L. F. Chem. Rev. (Washington, D.C.) 1996, 96, 115-136. (e) Denmark, S. E.; Thorarensen, A. Chem. Rev. (Washington, D.C.) 1996, 96, 137-165. (f) Winkler, J. D. Chem. Rev. (Washington, D.C.) 1996, 96, 167-176. (g) Ryu, I.; Sonoda, N.; Curran, D. P. Chem. Rev. (Washington, D.C.) 1996, 96, 177-194. (h) Parsons, P. J.; Penkett, C. S.; Shell, A. J. Chem. Rev. (Washington, D.C.) 1996, 96, 195-206. Wang, K. K. Chem. Rev. (Washington, D.C.) 1996, 96, 207-222. (j) Padwa, A.; Weingarten, M. D. Chem. Rev. (Washington, D.C.) 1996, 96, 223-269. (k) Harvey, D. F.; Sigano, D. M. Chem. Rev. (Washington, D.C.) 1996, 96, 271-288. Malacria, M. Chem. Rev. (Washington, D.C.) 1996, 96, 289-306. Molander, G. A.; Harris, C. R. Chem. Rev, (Washington, D.C.) 1996, 96, 307-338. (n) Snider, B. B. Chem. Rev. (Washington, D.C.) 1996, 96, 339-363. (o) Negishi, E.-i.; Copéret, C.; Ma, S.; Liou, S.-Y.; Liu, F. Chem. Rev. (Washington, D.C.) 1996, 96, 365-393. (p) Heumann, A.; Réglier, M. Tetrahedron 1996, 52, 9289-9346. (q) Bunce, R. A. Tetrahedron 1995, 51, 13103-13159. (r) Posner, G. H. Chem. Rev. (Washington, D.C.) 1986, 86, 831-844. (s) Skrydstrup, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 345-347.
10. For reviews and summaries of various processes, see (a) Ho, T.-L. Tandem Organic Reactions; Wiley-Interscience: New York; 1992. (b) Ho, T.-L. Tactics of Organic Synthesis; Wiley-Interscience: New York; 1994. Hudlicky, T. Chem. Rev. (Washington, D.C.) 1996, 96, 3-30. Tietze, L. F. Chem. Rev. (Washington, D.C.) 1996, 96, 115-136. (e) Denmark, S. E.; Thorarensen, A. Chem. Rev. (Washington, D.C.) 1996, 96, 137-165. (f) Winkler, J. D. Chem. Rev. (Washington, D.C.) 1996, 96, 167-176. (g) Ryu, I.; Sonoda, N.; Curran, D. P. Chem. Rev. (Washington, D.C.) 1996, 96, 177-194. (h) Parsons, P. J.; Penkett, C. S.; Shell, A. J. Chem. Rev. (Washington, D.C.) 1996, 96, 195-206. Wang, K. K. Chem. Rev. (Washington, D.C.) 1996, 96, 207-222. (j) Padwa, A.; Weingarten, M. D. Chem. Rev. (Washington, D.C.) 1996, 96, 223-269. (k) Harvey, D. F.; Sigano, D. M. Chem. Rev. (Washington, D.C.) 1996, 96, 271-288. Malacria, M. Chem. Rev. (Washington, D.C.) 1996, 96, 289-306. Molander, G. A.; Harris, C. R. Chem. Rev, (Washington, D.C.) 1996, 96, 307-338. (n) Snider, B. B. Chem. Rev. (Washington, D.C.) 1996, 96, 339-363. (o) Negishi, E.-i.; Copéret, C.; Ma, S.; Liou, S.-Y.; Liu, F. Chem. Rev. (Washington, D.C.) 1996, 96, 365-393. (p) Heumann, A.; Réglier, M. Tetrahedron 1996, 52, 9289-9346. (q) Bunce, R. A. Tetrahedron 1995, 51, 13103-13159. (r) Posner, G. H. Chem. Rev. (Washington, D.C.) 1986, 86, 831-844. (s) Skrydstrup, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 345-347.
11. For reviews and summaries of various processes, see (a) Ho, T.-L. Tandem Organic Reactions; Wiley-Interscience: New York; 1992. (b) Ho, T.-L. Tactics of Organic Synthesis; Wiley-Interscience: New York; 1994. Hudlicky, T. Chem. Rev. (Washington, D.C.) 1996, 96, 3-30. Tietze, L. F. Chem. Rev. (Washington, D.C.) 1996, 96, 115-136. (e) Denmark, S. E.; Thorarensen, A. Chem. Rev. (Washington, D.C.) 1996, 96, 137-165. (f) Winkler, J. D. Chem. Rev. (Washington, D.C.) 1996, 96, 167-176. (g) Ryu, I.; Sonoda, N.; Curran, D. P. Chem. Rev. (Washington, D.C.) 1996, 96, 177-194. (h) Parsons, P. J.; Penkett, C. S.; Shell, A. J. Chem. Rev. (Washington, D.C.) 1996, 96, 195-206. Wang, K. K. Chem. Rev. (Washington, D.C.) 1996, 96, 207-222. (j) Padwa, A.; Weingarten, M. D. Chem. Rev. (Washington, D.C.) 1996, 96, 223-269. (k) Harvey, D. F.; Sigano, D. M. Chem. Rev. (Washington, D.C.) 1996, 96, 271-288. Malacria, M. Chem. Rev. (Washington, D.C.) 1996, 96, 289-306. Molander, G. A.; Harris, C. R. Chem. Rev, (Washington, D.C.) 1996, 96, 307-338. (n) Snider, B. B. Chem. Rev. (Washington, D.C.) 1996, 96, 339-363. (o) Negishi, E.-i.; Copéret, C.; Ma, S.; Liou, S.-Y.; Liu, F. Chem. Rev. (Washington, D.C.) 1996, 96, 365-393. (p) Heumann, A.; Réglier, M. Tetrahedron 1996, 52, 9289-9346. (q) Bunce, R. A. Tetrahedron 1995, 51, 13103-13159. (r) Posner, G. H. Chem. Rev. (Washington, D.C.) 1986, 86, 831-844. (s) Skrydstrup, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 345-347.
12. For reviews and summaries of various processes, see (a) Ho, T.-L. Tandem Organic Reactions; Wiley-Interscience: New York; 1992. (b) Ho, T.-L. Tactics of Organic Synthesis; Wiley-Interscience: New York; 1994. Hudlicky, T. Chem. Rev. (Washington, D.C.) 1996, 96, 3-30. Tietze, L. F. Chem. Rev. (Washington, D.C.) 1996, 96, 115-136. (e) Denmark, S. E.; Thorarensen, A. Chem. Rev. (Washington, D.C.) 1996, 96, 137-165. (f) Winkler, J. D. Chem. Rev. (Washington, D.C.) 1996, 96, 167-176. (g) Ryu, I.; Sonoda, N.; Curran, D. P. Chem. Rev. (Washington, D.C.) 1996, 96, 177-194. (h) Parsons, P. J.; Penkett, C. S.; Shell, A. J. Chem. Rev. (Washington, D.C.) 1996, 96, 195-206. Wang, K. K. Chem. Rev. (Washington, D.C.) 1996, 96, 207-222. (j) Padwa, A.; Weingarten, M. D. Chem. Rev. (Washington, D.C.) 1996, 96, 223-269. (k) Harvey, D. F.; Sigano, D. M. Chem. Rev. (Washington, D.C.) 1996, 96, 271-288. Malacria, M. Chem. Rev. (Washington, D.C.) 1996, 96, 289-306. Molander, G. A.; Harris, C. R. Chem. Rev, (Washington, D.C.) 1996, 96, 307-338. (n) Snider, B. B. Chem. Rev. (Washington, D.C.) 1996, 96, 339-363. (o) Negishi, E.-i.; Copéret, C.; Ma, S.; Liou, S.-Y.; Liu, F. Chem. Rev. (Washington, D.C.) 1996, 96, 365-393. (p) Heumann, A.; Réglier, M. Tetrahedron 1996, 52, 9289-9346. (q) Bunce, R. A. Tetrahedron 1995, 51, 13103-13159. (r) Posner, G. H. Chem. Rev. (Washington, D.C.) 1986, 86, 831-844. (s) Skrydstrup, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 345-347.
13. For reviews and summaries of various processes, see (a) Ho, T.-L. Tandem Organic Reactions; Wiley-Interscience: New York; 1992. (b) Ho, T.-L. Tactics of Organic Synthesis; Wiley-Interscience: New York; 1994. Hudlicky, T. Chem. Rev. (Washington, D.C.) 1996, 96, 3-30. Tietze, L. F. Chem. Rev. (Washington, D.C.) 1996, 96, 115-136. (e) Denmark, S. E.; Thorarensen, A. Chem. Rev. (Washington, D.C.) 1996, 96, 137-165. (f) Winkler, J. D. Chem. Rev. (Washington, D.C.) 1996, 96, 167-176. (g) Ryu, I.; Sonoda, N.; Curran, D. P. Chem. Rev. (Washington, D.C.) 1996, 96, 177-194. (h) Parsons, P. J.; Penkett, C. S.; Shell, A. J. Chem. Rev. (Washington, D.C.) 1996, 96, 195-206. Wang, K. K. Chem. Rev. (Washington, D.C.) 1996, 96, 207-222. (j) Padwa, A.; Weingarten, M. D. Chem. Rev. (Washington, D.C.) 1996, 96, 223-269. (k) Harvey, D. F.; Sigano, D. M. Chem. Rev. (Washington, D.C.) 1996, 96, 271-288. Malacria, M. Chem. Rev. (Washington, D.C.) 1996, 96, 289-306. Molander, G. A.; Harris, C. R. Chem. Rev, (Washington, D.C.) 1996, 96, 307-338. (n) Snider, B. B. Chem. Rev. (Washington, D.C.) 1996, 96, 339-363. (o) Negishi, E.-i.; Copéret, C.; Ma, S.; Liou, S.-Y.; Liu, F. Chem. Rev. (Washington, D.C.) 1996, 96, 365-393. (p) Heumann, A.; Réglier, M. Tetrahedron 1996, 52, 9289-9346. (q) Bunce, R. A. Tetrahedron 1995, 51, 13103-13159. (r) Posner, G. H. Chem. Rev. (Washington, D.C.) 1986, 86, 831-844. (s) Skrydstrup, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 345-347.
14. For reviews and summaries of various processes, see (a) Ho, T.-L. Tandem Organic Reactions; Wiley-Interscience: New York; 1992. (b) Ho, T.-L. Tactics of Organic Synthesis; Wiley-Interscience: New York; 1994. Hudlicky, T. Chem. Rev. (Washington, D.C.) 1996, 96, 3-30. Tietze, L. F. Chem. Rev. (Washington, D.C.) 1996, 96, 115-136. (e) Denmark, S. E.; Thorarensen, A. Chem. Rev. (Washington, D.C.) 1996, 96, 137-165. (f) Winkler, J. D. Chem. Rev. (Washington, D.C.) 1996, 96, 167-176. (g) Ryu, I.; Sonoda, N.; Curran, D. P. Chem. Rev. (Washington, D.C.) 1996, 96, 177-194. (h) Parsons, P. J.; Penkett, C. S.; Shell, A. J. Chem. Rev. (Washington, D.C.) 1996, 96, 195-206. Wang, K. K. Chem. Rev. (Washington, D.C.) 1996, 96, 207-222. (j) Padwa, A.; Weingarten, M. D. Chem. Rev. (Washington, D.C.) 1996, 96, 223-269. (k) Harvey, D. F.; Sigano, D. M. Chem. Rev. (Washington, D.C.) 1996, 96, 271-288. Malacria, M. Chem. Rev. (Washington, D.C.) 1996, 96, 289-306. Molander, G. A.; Harris, C. R. Chem. Rev, (Washington, D.C.) 1996, 96, 307-338. (n) Snider, B. B. Chem. Rev. (Washington, D.C.) 1996, 96, 339-363. (o) Negishi, E.-i.; Copéret, C.; Ma, S.; Liou, S.-Y.; Liu, F. Chem. Rev. (Washington, D.C.) 1996, 96, 365-393. (p) Heumann, A.; Réglier, M. Tetrahedron 1996, 52, 9289-9346. (q) Bunce, R. A. Tetrahedron 1995, 51, 13103-13159. (r) Posner, G. H. Chem. Rev. (Washington, D.C.) 1986, 86, 831-844. (s) Skrydstrup, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 345-347.
15. For reviews and summaries of various processes, see (a) Ho, T.-L. Tandem Organic Reactions; Wiley-Interscience: New York; 1992. (b) Ho, T.-L. Tactics of Organic Synthesis; Wiley-Interscience: New York; 1994. Hudlicky, T. Chem. Rev. (Washington, D.C.) 1996, 96, 3-30. Tietze, L. F. Chem. Rev. (Washington, D.C.) 1996, 96, 115-136. (e) Denmark, S. E.; Thorarensen, A. Chem. Rev. (Washington, D.C.) 1996, 96, 137-165. (f) Winkler, J. D. Chem. Rev. (Washington, D.C.) 1996, 96, 167-176. (g) Ryu, I.; Sonoda, N.; Curran, D. P. Chem. Rev. (Washington, D.C.) 1996, 96, 177-194. (h) Parsons, P. J.; Penkett, C. S.; Shell, A. J. Chem. Rev. (Washington, D.C.) 1996, 96, 195-206. Wang, K. K. Chem. Rev. (Washington, D.C.) 1996, 96, 207-222. (j) Padwa, A.; Weingarten, M. D. Chem. Rev. (Washington, D.C.) 1996, 96, 223-269. (k) Harvey, D. F.; Sigano, D. M. Chem. Rev. (Washington, D.C.) 1996, 96, 271-288. Malacria, M. Chem. Rev. (Washington, D.C.) 1996, 96, 289-306. Molander, G. A.; Harris, C. R. Chem. Rev, (Washington, D.C.) 1996, 96, 307-338. (n) Snider, B. B. Chem. Rev. (Washington, D.C.) 1996, 96, 339-363. (o) Negishi, E.-i.; Copéret, C.; Ma, S.; Liou, S.-Y.; Liu, F. Chem. Rev. (Washington, D.C.) 1996, 96, 365-393. (p) Heumann, A.; Réglier, M. Tetrahedron 1996, 52, 9289-9346. (q) Bunce, R. A. Tetrahedron 1995, 51, 13103-13159. (r) Posner, G. H. Chem. Rev. (Washington, D.C.) 1986, 86, 831-844. (s) Skrydstrup, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 345-347.
16. For reviews and summaries of various processes, see (a) Ho, T.-L. Tandem Organic Reactions; Wiley-Interscience: New York; 1992. (b) Ho, T.-L. Tactics of Organic Synthesis; Wiley-Interscience: New York; 1994. Hudlicky, T. Chem. Rev. (Washington, D.C.) 1996, 96, 3-30. Tietze, L. F. Chem. Rev. (Washington, D.C.) 1996, 96, 115-136. (e) Denmark, S. E.; Thorarensen, A. Chem. Rev. (Washington, D.C.) 1996, 96, 137-165. (f) Winkler, J. D. Chem. Rev. (Washington, D.C.) 1996, 96, 167-176. (g) Ryu, I.; Sonoda, N.; Curran, D. P. Chem. Rev. (Washington, D.C.) 1996, 96, 177-194. (h) Parsons, P. J.; Penkett, C. S.; Shell, A. J. Chem. Rev. (Washington, D.C.) 1996, 96, 195-206. Wang, K. K. Chem. Rev. (Washington, D.C.) 1996, 96, 207-222. (j) Padwa, A.; Weingarten, M. D. Chem. Rev. (Washington, D.C.) 1996, 96, 223-269. (k) Harvey, D. F.; Sigano, D. M. Chem. Rev. (Washington, D.C.) 1996, 96, 271-288. Malacria, M. Chem. Rev. (Washington, D.C.) 1996, 96, 289-306. Molander, G. A.; Harris, C. R. Chem. Rev, (Washington, D.C.) 1996, 96, 307-338. (n) Snider, B. B. Chem. Rev. (Washington, D.C.) 1996, 96, 339-363. (o) Negishi, E.-i.; Copéret, C.; Ma, S.; Liou, S.-Y.; Liu, F. Chem. Rev. (Washington, D.C.) 1996, 96, 365-393. (p) Heumann, A.; Réglier, M. Tetrahedron 1996, 52, 9289-9346. (q) Bunce, R. A. Tetrahedron 1995, 51, 13103-13159. (r) Posner, G. H. Chem. Rev. (Washington, D.C.) 1986, 86, 831-844. (s) Skrydstrup, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 345-347.
17. For reviews and summaries of various processes, see (a) Ho, T.-L. Tandem Organic Reactions; Wiley-Interscience: New York; 1992. (b) Ho, T.-L. Tactics of Organic Synthesis; Wiley-Interscience: New York; 1994. Hudlicky, T. Chem. Rev. (Washington, D.C.) 1996, 96, 3-30. Tietze, L. F. Chem. Rev. (Washington, D.C.) 1996, 96, 115-136. (e) Denmark, S. E.; Thorarensen, A. Chem. Rev. (Washington, D.C.) 1996, 96, 137-165. (f) Winkler, J. D. Chem. Rev. (Washington, D.C.) 1996, 96, 167-176. (g) Ryu, I.; Sonoda, N.; Curran, D. P. Chem. Rev. (Washington, D.C.) 1996, 96, 177-194. (h) Parsons, P. J.; Penkett, C. S.; Shell, A. J. Chem. Rev. (Washington, D.C.) 1996, 96, 195-206. Wang, K. K. Chem. Rev. (Washington, D.C.) 1996, 96, 207-222. (j) Padwa, A.; Weingarten, M. D. Chem. Rev. (Washington, D.C.) 1996, 96, 223-269. (k) Harvey, D. F.; Sigano, D. M. Chem. Rev. (Washington, D.C.) 1996, 96, 271-288. Malacria, M. Chem. Rev. (Washington, D.C.) 1996, 96, 289-306. Molander, G. A.; Harris, C. R. Chem. Rev, (Washington, D.C.) 1996, 96, 307-338. (n) Snider, B. B. Chem. Rev. (Washington, D.C.) 1996, 96, 339-363. (o) Negishi, E.-i.; Copéret, C.; Ma, S.; Liou, S.-Y.; Liu, F. Chem. Rev. (Washington, D.C.) 1996, 96, 365-393. (p) Heumann, A.; Réglier, M. Tetrahedron 1996, 52, 9289-9346. (q) Bunce, R. A. Tetrahedron 1995, 51, 13103-13159. (r) Posner, G. H. Chem. Rev. (Washington, D.C.) 1986, 86, 831-844. (s) Skrydstrup, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 345-347.
18. For reviews and summaries of various processes, see (a) Ho, T.-L. Tandem Organic Reactions; Wiley-Interscience: New York; 1992. (b) Ho, T.-L. Tactics of Organic Synthesis; Wiley-Interscience: New York; 1994. Hudlicky, T. Chem. Rev. (Washington, D.C.) 1996, 96, 3-30. Tietze, L. F. Chem. Rev. (Washington, D.C.) 1996, 96, 115-136. (e) Denmark, S. E.; Thorarensen, A. Chem. Rev. (Washington, D.C.) 1996, 96, 137-165. (f) Winkler, J. D. Chem. Rev. (Washington, D.C.) 1996, 96, 167-176. (g) Ryu, I.; Sonoda, N.; Curran, D. P. Chem. Rev. (Washington, D.C.) 1996, 96, 177-194. (h) Parsons, P. J.; Penkett, C. S.; Shell, A. J. Chem. Rev. (Washington, D.C.) 1996, 96, 195-206. Wang, K. K. Chem. Rev. (Washington, D.C.) 1996, 96, 207-222. (j) Padwa, A.; Weingarten, M. D. Chem. Rev. (Washington, D.C.) 1996, 96, 223-269. (k) Harvey, D. F.; Sigano, D. M. Chem. Rev. (Washington, D.C.) 1996, 96, 271-288. Malacria, M. Chem. Rev. (Washington, D.C.) 1996, 96, 289-306. Molander, G. A.; Harris, C. R. Chem. Rev, (Washington, D.C.) 1996, 96, 307-338. (n) Snider, B. B. Chem. Rev. (Washington, D.C.) 1996, 96, 339-363. (o) Negishi, E.-i.; Copéret, C.; Ma, S.; Liou, S.-Y.; Liu, F. Chem. Rev. (Washington, D.C.) 1996, 96, 365-393. (p) Heumann, A.; Réglier, M. Tetrahedron 1996, 52, 9289-9346. (q) Bunce, R. A. Tetrahedron 1995, 51, 13103-13159. (r) Posner, G. H. Chem. Rev. (Washington, D.C.) 1986, 86, 831-844. (s) Skrydstrup, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 345-347.
19. For reviews and summaries of various processes, see (a) Ho, T.-L. Tandem Organic Reactions; Wiley-Interscience: New York; 1992. (b) Ho, T.-L. Tactics of Organic Synthesis; Wiley-Interscience: New York; 1994. Hudlicky, T. Chem. Rev. (Washington, D.C.) 1996, 96, 3-30. Tietze, L. F. Chem. Rev. (Washington, D.C.) 1996, 96, 115-136. (e) Denmark, S. E.; Thorarensen, A. Chem. Rev. (Washington, D.C.) 1996, 96, 137-165. (f) Winkler, J. D. Chem. Rev. (Washington, D.C.) 1996, 96, 167-176. (g) Ryu, I.; Sonoda, N.; Curran, D. P. Chem. Rev. (Washington, D.C.) 1996, 96, 177-194. (h) Parsons, P. J.; Penkett, C. S.; Shell, A. J. Chem. Rev. (Washington, D.C.) 1996, 96, 195-206. Wang, K. K. Chem. Rev. (Washington, D.C.) 1996, 96, 207-222. (j) Padwa, A.; Weingarten, M. D. Chem. Rev. (Washington, D.C.) 1996, 96, 223-269. (k) Harvey, D. F.; Sigano, D. M. Chem. Rev. (Washington, D.C.) 1996, 96, 271-288. Malacria, M. Chem. Rev. (Washington, D.C.) 1996, 96, 289-306. Molander, G. A.; Harris, C. R. Chem. Rev, (Washington, D.C.) 1996, 96, 307-338. (n) Snider, B. B. Chem. Rev. (Washington, D.C.) 1996, 96, 339-363. (o) Negishi, E.-i.; Copéret, C.; Ma, S.; Liou, S.-Y.; Liu, F. Chem. Rev. (Washington, D.C.) 1996, 96, 365-393. (p) Heumann, A.; Réglier, M. Tetrahedron 1996, 52, 9289-9346. (q) Bunce, R. A. Tetrahedron 1995, 51, 13103-13159. (r) Posner, G. H. Chem. Rev. (Washington, D.C.) 1986, 86, 831-844. (s) Skrydstrup, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 345-347.
20. For selected representative recent reports of specific processes, with references to extensive literature, see (a) Nakamura, E.; Kubota, K.; Sakata, G. J. Am. Chem. Soc. 1997, 119, 5457-5458. (b) Grigg, R.; Rasul, R.; Savic, V. Tetrahedron Lett. 1997, 38, 1825-1828. Grigg, R.; Loganathan, V.; Sridharan, V. Tetrahedron Lett. 1996, 37, 3399-3402. Yamada, H.; Aoyagi, S.; Kibayashi, C. Tetrahedron Lett. 1997, 38, 3027-3030. (e) Markó, I. E.; Mekhalfia, A.; Murphy, F.; Bayston, D. J.; Bailey, M.; Janousek, Z.; Dolan, S. Pure Appl. Chem. 1997, 69, 565-570. (f) Fillery, S. F.; Gordon, G. J.; Luker, T.; Whitby, R. J. Pure Appl. Chem. 1997, 69, 633-638. (g) Fish, P. V.; Johnson, W. S. J. Org. Chem. 1994, 59, 2324-2335. (h) Fish, P. V.; Johnson, W. S.; Jones, G. S.; Tham, F. S.; Kullnig, R. K. J. Org. Chem. 1994, 59, 6150-6152. Lautens, M.; Fillion, E. J. Org. Chem. 1997, 62, 4418-4427. (j) Organ, M. G.; Winkle, D. D.; Huffmann, J. J. Org. Chem. 1997, 62, 5254-5266. (k) Paquette, L. A.; Kuo, L. H.; Doyon, J. J. Am. Chem. Soc. 1997, 119, 3038-3047. Davies, H. M. L.; Ahmed, G.; Churchill, M. R. J. Am. Chem. Soc. 1996, 118, 10774-10782. Pearson, W. H.; Mi, Y. Tetrahedron Lett. 1997, 38, 5441-5444.
21. For selected representative recent reports of specific processes, with references to extensive literature, see (a) Nakamura, E.; Kubota, K.; Sakata, G. J. Am. Chem. Soc. 1997, 119, 5457-5458. (b) Grigg, R.; Rasul, R.; Savic, V. Tetrahedron Lett. 1997, 38, 1825-1828. Grigg, R.; Loganathan, V.; Sridharan, V. Tetrahedron Lett. 1996, 37, 3399-3402. Yamada, H.; Aoyagi, S.; Kibayashi, C. Tetrahedron Lett. 1997, 38, 3027-3030. (e) Markó, I. E.; Mekhalfia, A.; Murphy, F.; Bayston, D. J.; Bailey, M.; Janousek, Z.; Dolan, S. Pure Appl. Chem. 1997, 69, 565-570. (f) Fillery, S. F.; Gordon, G. J.; Luker, T.; Whitby, R. J. Pure Appl. Chem. 1997, 69, 633-638. (g) Fish, P. V.; Johnson, W. S. J. Org. Chem. 1994, 59, 2324-2335. (h) Fish, P. V.; Johnson, W. S.; Jones, G. S.; Tham, F. S.; Kullnig, R. K. J. Org. Chem. 1994, 59, 6150-6152. Lautens, M.; Fillion, E. J. Org. Chem. 1997, 62, 4418-4427. (j) Organ, M. G.; Winkle, D. D.; Huffmann, J. J. Org. Chem. 1997, 62, 5254-5266. (k) Paquette, L. A.; Kuo, L. H.; Doyon, J. J. Am. Chem. Soc. 1997, 119, 3038-3047. Davies, H. M. L.; Ahmed, G.; Churchill, M. R. J. Am. Chem. Soc. 1996, 118, 10774-10782. Pearson, W. H.; Mi, Y. Tetrahedron Lett. 1997, 38, 5441-5444.
22. For selected representative recent reports of specific processes, with references to extensive literature, see (a) Nakamura, E.; Kubota, K.; Sakata, G. J. Am. Chem. Soc. 1997, 119, 5457-5458. (b) Grigg, R.; Rasul, R.; Savic, V. Tetrahedron Lett. 1997, 38, 1825-1828. Grigg, R.; Loganathan, V.; Sridharan, V. Tetrahedron Lett. 1996, 37, 3399-3402. Yamada, H.; Aoyagi, S.; Kibayashi, C. Tetrahedron Lett. 1997, 38, 3027-3030. (e) Markó, I. E.; Mekhalfia, A.; Murphy, F.; Bayston, D. J.; Bailey, M.; Janousek, Z.; Dolan, S. Pure Appl. Chem. 1997, 69, 565-570. (f) Fillery, S. F.; Gordon, G. J.; Luker, T.; Whitby, R. J. Pure Appl. Chem. 1997, 69, 633-638. (g) Fish, P. V.; Johnson, W. S. J. Org. Chem. 1994, 59, 2324-2335. (h) Fish, P. V.; Johnson, W. S.; Jones, G. S.; Tham, F. S.; Kullnig, R. K. J. Org. Chem. 1994, 59, 6150-6152. Lautens, M.; Fillion, E. J. Org. Chem. 1997, 62, 4418-4427. (j) Organ, M. G.; Winkle, D. D.; Huffmann, J. J. Org. Chem. 1997, 62, 5254-5266. (k) Paquette, L. A.; Kuo, L. H.; Doyon, J. J. Am. Chem. Soc. 1997, 119, 3038-3047. Davies, H. M. L.; Ahmed, G.; Churchill, M. R. J. Am. Chem. Soc. 1996, 118, 10774-10782. Pearson, W. H.; Mi, Y. Tetrahedron Lett. 1997, 38, 5441-5444.
23. For selected representative recent reports of specific processes, with references to extensive literature, see (a) Nakamura, E.; Kubota, K.; Sakata, G. J. Am. Chem. Soc. 1997, 119, 5457-5458. (b) Grigg, R.; Rasul, R.; Savic, V. Tetrahedron Lett. 1997, 38, 1825-1828. Grigg, R.; Loganathan, V.; Sridharan, V. Tetrahedron Lett. 1996, 37, 3399-3402. Yamada, H.; Aoyagi, S.; Kibayashi, C. Tetrahedron Lett. 1997, 38, 3027-3030. (e) Markó, I. E.; Mekhalfia, A.; Murphy, F.; Bayston, D. J.; Bailey, M.; Janousek, Z.; Dolan, S. Pure Appl. Chem. 1997, 69, 565-570. (f) Fillery, S. F.; Gordon, G. J.; Luker, T.; Whitby, R. J. Pure Appl. Chem. 1997, 69, 633-638. (g) Fish, P. V.; Johnson, W. S. J. Org. Chem. 1994, 59, 2324-2335. (h) Fish, P. V.; Johnson, W. S.; Jones, G. S.; Tham, F. S.; Kullnig, R. K. J. Org. Chem. 1994, 59, 6150-6152. Lautens, M.; Fillion, E. J. Org. Chem. 1997, 62, 4418-4427. (j) Organ, M. G.; Winkle, D. D.; Huffmann, J. J. Org. Chem. 1997, 62, 5254-5266. (k) Paquette, L. A.; Kuo, L. H.; Doyon, J. J. Am. Chem. Soc. 1997, 119, 3038-3047. Davies, H. M. L.; Ahmed, G.; Churchill, M. R. J. Am. Chem. Soc. 1996, 118, 10774-10782. Pearson, W. H.; Mi, Y. Tetrahedron Lett. 1997, 38, 5441-5444.
24. For selected representative recent reports of specific processes, with references to extensive literature, see (a) Nakamura, E.; Kubota, K.; Sakata, G. J. Am. Chem. Soc. 1997, 119, 5457-5458. (b) Grigg, R.; Rasul, R.; Savic, V. Tetrahedron Lett. 1997, 38, 1825-1828. Grigg, R.; Loganathan, V.; Sridharan, V. Tetrahedron Lett. 1996, 37, 3399-3402. Yamada, H.; Aoyagi, S.; Kibayashi, C. Tetrahedron Lett. 1997, 38, 3027-3030. (e) Markó, I. E.; Mekhalfia, A.; Murphy, F.; Bayston, D. J.; Bailey, M.; Janousek, Z.; Dolan, S. Pure Appl. Chem. 1997, 69, 565-570. (f) Fillery, S. F.; Gordon, G. J.; Luker, T.; Whitby, R. J. Pure Appl. Chem. 1997, 69, 633-638. (g) Fish, P. V.; Johnson, W. S. J. Org. Chem. 1994, 59, 2324-2335. (h) Fish, P. V.; Johnson, W. S.; Jones, G. S.; Tham, F. S.; Kullnig, R. K. J. Org. Chem. 1994, 59, 6150-6152. Lautens, M.; Fillion, E. J. Org. Chem. 1997, 62, 4418-4427. (j) Organ, M. G.; Winkle, D. D.; Huffmann, J. J. Org. Chem. 1997, 62, 5254-5266. (k) Paquette, L. A.; Kuo, L. H.; Doyon, J. J. Am. Chem. Soc. 1997, 119, 3038-3047. Davies, H. M. L.; Ahmed, G.; Churchill, M. R. J. Am. Chem. Soc. 1996, 118, 10774-10782. Pearson, W. H.; Mi, Y. Tetrahedron Lett. 1997, 38, 5441-5444.
25. For selected representative recent reports of specific processes, with references to extensive literature, see (a) Nakamura, E.; Kubota, K.; Sakata, G. J. Am. Chem. Soc. 1997, 119, 5457-5458. (b) Grigg, R.; Rasul, R.; Savic, V. Tetrahedron Lett. 1997, 38, 1825-1828. Grigg, R.; Loganathan, V.; Sridharan, V. Tetrahedron Lett. 1996, 37, 3399-3402. Yamada, H.; Aoyagi, S.; Kibayashi, C. Tetrahedron Lett. 1997, 38, 3027-3030. (e) Markó, I. E.; Mekhalfia, A.; Murphy, F.; Bayston, D. J.; Bailey, M.; Janousek, Z.; Dolan, S. Pure Appl. Chem. 1997, 69, 565-570. (f) Fillery, S. F.; Gordon, G. J.; Luker, T.; Whitby, R. J. Pure Appl. Chem. 1997, 69, 633-638. (g) Fish, P. V.; Johnson, W. S. J. Org. Chem. 1994, 59, 2324-2335. (h) Fish, P. V.; Johnson, W. S.; Jones, G. S.; Tham, F. S.; Kullnig, R. K. J. Org. Chem. 1994, 59, 6150-6152. Lautens, M.; Fillion, E. J. Org. Chem. 1997, 62, 4418-4427. (j) Organ, M. G.; Winkle, D. D.; Huffmann, J. J. Org. Chem. 1997, 62, 5254-5266. (k) Paquette, L. A.; Kuo, L. H.; Doyon, J. J. Am. Chem. Soc. 1997, 119, 3038-3047. Davies, H. M. L.; Ahmed, G.; Churchill, M. R. J. Am. Chem. Soc. 1996, 118, 10774-10782. Pearson, W. H.; Mi, Y. Tetrahedron Lett. 1997, 38, 5441-5444.
26. For selected representative recent reports of specific processes, with references to extensive literature, see (a) Nakamura, E.; Kubota, K.; Sakata, G. J. Am. Chem. Soc. 1997, 119, 5457-5458. (b) Grigg, R.; Rasul, R.; Savic, V. Tetrahedron Lett. 1997, 38, 1825-1828. Grigg, R.; Loganathan, V.; Sridharan, V. Tetrahedron Lett. 1996, 37, 3399-3402. Yamada, H.; Aoyagi, S.; Kibayashi, C. Tetrahedron Lett. 1997, 38, 3027-3030. (e) Markó, I. E.; Mekhalfia, A.; Murphy, F.; Bayston, D. J.; Bailey, M.; Janousek, Z.; Dolan, S. Pure Appl. Chem. 1997, 69, 565-570. (f) Fillery, S. F.; Gordon, G. J.; Luker, T.; Whitby, R. J. Pure Appl. Chem. 1997, 69, 633-638. (g) Fish, P. V.; Johnson, W. S. J. Org. Chem. 1994, 59, 2324-2335. (h) Fish, P. V.; Johnson, W. S.; Jones, G. S.; Tham, F. S.; Kullnig, R. K. J. Org. Chem. 1994, 59, 6150-6152. Lautens, M.; Fillion, E. J. Org. Chem. 1997, 62, 4418-4427. (j) Organ, M. G.; Winkle, D. D.; Huffmann, J. J. Org. Chem. 1997, 62, 5254-5266. (k) Paquette, L. A.; Kuo, L. H.; Doyon, J. J. Am. Chem. Soc. 1997, 119, 3038-3047. Davies, H. M. L.; Ahmed, G.; Churchill, M. R. J. Am. Chem. Soc. 1996, 118, 10774-10782. Pearson, W. H.; Mi, Y. Tetrahedron Lett. 1997, 38, 5441-5444.
27. For selected representative recent reports of specific processes, with references to extensive literature, see (a) Nakamura, E.; Kubota, K.; Sakata, G. J. Am. Chem. Soc. 1997, 119, 5457-5458. (b) Grigg, R.; Rasul, R.; Savic, V. Tetrahedron Lett. 1997, 38, 1825-1828. Grigg, R.; Loganathan, V.; Sridharan, V. Tetrahedron Lett. 1996, 37, 3399-3402. Yamada, H.; Aoyagi, S.; Kibayashi, C. Tetrahedron Lett. 1997, 38, 3027-3030. (e) Markó, I. E.; Mekhalfia, A.; Murphy, F.; Bayston, D. J.; Bailey, M.; Janousek, Z.; Dolan, S. Pure Appl. Chem. 1997, 69, 565-570. (f) Fillery, S. F.; Gordon, G. J.; Luker, T.; Whitby, R. J. Pure Appl. Chem. 1997, 69, 633-638. (g) Fish, P. V.; Johnson, W. S. J. Org. Chem. 1994, 59, 2324-2335. (h) Fish, P. V.; Johnson, W. S.; Jones, G. S.; Tham, F. S.; Kullnig, R. K. J. Org. Chem. 1994, 59, 6150-6152. Lautens, M.; Fillion, E. J. Org. Chem. 1997, 62, 4418-4427. (j) Organ, M. G.; Winkle, D. D.; Huffmann, J. J. Org. Chem. 1997, 62, 5254-5266. (k) Paquette, L. A.; Kuo, L. H.; Doyon, J. J. Am. Chem. Soc. 1997, 119, 3038-3047. Davies, H. M. L.; Ahmed, G.; Churchill, M. R. J. Am. Chem. Soc. 1996, 118, 10774-10782. Pearson, W. H.; Mi, Y. Tetrahedron Lett. 1997, 38, 5441-5444.
28. For selected representative recent reports of specific processes, with references to extensive literature, see (a) Nakamura, E.; Kubota, K.; Sakata, G. J. Am. Chem. Soc. 1997, 119, 5457-5458. (b) Grigg, R.; Rasul, R.; Savic, V. Tetrahedron Lett. 1997, 38, 1825-1828. Grigg, R.; Loganathan, V.; Sridharan, V. Tetrahedron Lett. 1996, 37, 3399-3402. Yamada, H.; Aoyagi, S.; Kibayashi, C. Tetrahedron Lett. 1997, 38, 3027-3030. (e) Markó, I. E.; Mekhalfia, A.; Murphy, F.; Bayston, D. J.; Bailey, M.; Janousek, Z.; Dolan, S. Pure Appl. Chem. 1997, 69, 565-570. (f) Fillery, S. F.; Gordon, G. J.; Luker, T.; Whitby, R. J. Pure Appl. Chem. 1997, 69, 633-638. (g) Fish, P. V.; Johnson, W. S. J. Org. Chem. 1994, 59, 2324-2335. (h) Fish, P. V.; Johnson, W. S.; Jones, G. S.; Tham, F. S.; Kullnig, R. K. J. Org. Chem. 1994, 59, 6150-6152. Lautens, M.; Fillion, E. J. Org. Chem. 1997, 62, 4418-4427. (j) Organ, M. G.; Winkle, D. D.; Huffmann, J. J. Org. Chem. 1997, 62, 5254-5266. (k) Paquette, L. A.; Kuo, L. H.; Doyon, J. J. Am. Chem. Soc. 1997, 119, 3038-3047. Davies, H. M. L.; Ahmed, G.; Churchill, M. R. J. Am. Chem. Soc. 1996, 118, 10774-10782. Pearson, W. H.; Mi, Y. Tetrahedron Lett. 1997, 38, 5441-5444.
29. For selected representative recent reports of specific processes, with references to extensive literature, see (a) Nakamura, E.; Kubota, K.; Sakata, G. J. Am. Chem. Soc. 1997, 119, 5457-5458. (b) Grigg, R.; Rasul, R.; Savic, V. Tetrahedron Lett. 1997, 38, 1825-1828. Grigg, R.; Loganathan, V.; Sridharan, V. Tetrahedron Lett. 1996, 37, 3399-3402. Yamada, H.; Aoyagi, S.; Kibayashi, C. Tetrahedron Lett. 1997, 38, 3027-3030. (e) Markó, I. E.; Mekhalfia, A.; Murphy, F.; Bayston, D. J.; Bailey, M.; Janousek, Z.; Dolan, S. Pure Appl. Chem. 1997, 69, 565-570. (f) Fillery, S. F.; Gordon, G. J.; Luker, T.; Whitby, R. J. Pure Appl. Chem. 1997, 69, 633-638. (g) Fish, P. V.; Johnson, W. S. J. Org. Chem. 1994, 59, 2324-2335. (h) Fish, P. V.; Johnson, W. S.; Jones, G. S.; Tham, F. S.; Kullnig, R. K. J. Org. Chem. 1994, 59, 6150-6152. Lautens, M.; Fillion, E. J. Org. Chem. 1997, 62, 4418-4427. (j) Organ, M. G.; Winkle, D. D.; Huffmann, J. J. Org. Chem. 1997, 62, 5254-5266. (k) Paquette, L. A.; Kuo, L. H.; Doyon, J. J. Am. Chem. Soc. 1997, 119, 3038-3047. Davies, H. M. L.; Ahmed, G.; Churchill, M. R. J. Am. Chem. Soc. 1996, 118, 10774-10782. Pearson, W. H.; Mi, Y. Tetrahedron Lett. 1997, 38, 5441-5444.
30. For selected representative recent reports of specific processes, with references to extensive literature, see (a) Nakamura, E.; Kubota, K.; Sakata, G. J. Am. Chem. Soc. 1997, 119, 5457-5458. (b) Grigg, R.; Rasul, R.; Savic, V. Tetrahedron Lett. 1997, 38, 1825-1828. Grigg, R.; Loganathan, V.; Sridharan, V. Tetrahedron Lett. 1996, 37, 3399-3402. Yamada, H.; Aoyagi, S.; Kibayashi, C. Tetrahedron Lett. 1997, 38, 3027-3030. (e) Markó, I. E.; Mekhalfia, A.; Murphy, F.; Bayston, D. J.; Bailey, M.; Janousek, Z.; Dolan, S. Pure Appl. Chem. 1997, 69, 565-570. (f) Fillery, S. F.; Gordon, G. J.; Luker, T.; Whitby, R. J. Pure Appl. Chem. 1997, 69, 633-638. (g) Fish, P. V.; Johnson, W. S. J. Org. Chem. 1994, 59, 2324-2335. (h) Fish, P. V.; Johnson, W. S.; Jones, G. S.; Tham, F. S.; Kullnig, R. K. J. Org. Chem. 1994, 59, 6150-6152. Lautens, M.; Fillion, E. J. Org. Chem. 1997, 62, 4418-4427. (j) Organ, M. G.; Winkle, D. D.; Huffmann, J. J. Org. Chem. 1997, 62, 5254-5266. (k) Paquette, L. A.; Kuo, L. H.; Doyon, J. J. Am. Chem. Soc. 1997, 119, 3038-3047. Davies, H. M. L.; Ahmed, G.; Churchill, M. R. J. Am. Chem. Soc. 1996, 118, 10774-10782. Pearson, W. H.; Mi, Y. Tetrahedron Lett. 1997, 38, 5441-5444.
31. For selected representative recent reports of specific processes, with references to extensive literature, see (a) Nakamura, E.; Kubota, K.; Sakata, G. J. Am. Chem. Soc. 1997, 119, 5457-5458. (b) Grigg, R.; Rasul, R.; Savic, V. Tetrahedron Lett. 1997, 38, 1825-1828. Grigg, R.; Loganathan, V.; Sridharan, V. Tetrahedron Lett. 1996, 37, 3399-3402. Yamada, H.; Aoyagi, S.; Kibayashi, C. Tetrahedron Lett. 1997, 38, 3027-3030. (e) Markó, I. E.; Mekhalfia, A.; Murphy, F.; Bayston, D. J.; Bailey, M.; Janousek, Z.; Dolan, S. Pure Appl. Chem. 1997, 69, 565-570. (f) Fillery, S. F.; Gordon, G. J.; Luker, T.; Whitby, R. J. Pure Appl. Chem. 1997, 69, 633-638. (g) Fish, P. V.; Johnson, W. S. J. Org. Chem. 1994, 59, 2324-2335. (h) Fish, P. V.; Johnson, W. S.; Jones, G. S.; Tham, F. S.; Kullnig, R. K. J. Org. Chem. 1994, 59, 6150-6152. Lautens, M.; Fillion, E. J. Org. Chem. 1997, 62, 4418-4427. (j) Organ, M. G.; Winkle, D. D.; Huffmann, J. J. Org. Chem. 1997, 62, 5254-5266. (k) Paquette, L. A.; Kuo, L. H.; Doyon, J. J. Am. Chem. Soc. 1997, 119, 3038-3047. Davies, H. M. L.; Ahmed, G.; Churchill, M. R. J. Am. Chem. Soc. 1996, 118, 10774-10782. Pearson, W. H.; Mi, Y. Tetrahedron Lett. 1997, 38, 5441-5444.
32. For selected representative recent reports of specific processes, with references to extensive literature, see (a) Nakamura, E.; Kubota, K.; Sakata, G. J. Am. Chem. Soc. 1997, 119, 5457-5458. (b) Grigg, R.; Rasul, R.; Savic, V. Tetrahedron Lett. 1997, 38, 1825-1828. Grigg, R.; Loganathan, V.; Sridharan, V. Tetrahedron Lett. 1996, 37, 3399-3402. Yamada, H.; Aoyagi, S.; Kibayashi, C. Tetrahedron Lett. 1997, 38, 3027-3030. (e) Markó, I. E.; Mekhalfia, A.; Murphy, F.; Bayston, D. J.; Bailey, M.; Janousek, Z.; Dolan, S. Pure Appl. Chem. 1997, 69, 565-570. (f) Fillery, S. F.; Gordon, G. J.; Luker, T.; Whitby, R. J. Pure Appl. Chem. 1997, 69, 633-638. (g) Fish, P. V.; Johnson, W. S. J. Org. Chem. 1994, 59, 2324-2335. (h) Fish, P. V.; Johnson, W. S.; Jones, G. S.; Tham, F. S.; Kullnig, R. K. J. Org. Chem. 1994, 59, 6150-6152. Lautens, M.; Fillion, E. J. Org. Chem. 1997, 62, 4418-4427. (j) Organ, M. G.; Winkle, D. D.; Huffmann, J. J. Org. Chem. 1997, 62, 5254-5266. (k) Paquette, L. A.; Kuo, L. H.; Doyon, J. J. Am. Chem. Soc. 1997, 119, 3038-3047. Davies, H. M. L.; Ahmed, G.; Churchill, M. R. J. Am. Chem. Soc. 1996, 118, 10774-10782. Pearson, W. H.; Mi, Y. Tetrahedron Lett. 1997, 38, 5441-5444.
33. (a) Engler, T. A.; Combrink, K. D.; Letavic, M. A.; Lynch, K. O., Jr.; Ray, J. E. J. Org. Chem. 1994, 59, 6567-6587.
34. (b) Engler, T. A.; Wei, D.; Letavic, M. A.; Combrink, K. D.; Reddy, J. P. J. Org. Chem. 1994, 59, 6588-6599.
35. 5 + 2 Cycloadducts are also found in reactions of quinone monoand bis-imides: (a) Engler, T. A.; Meduna, S. P.; LaTessa, K. O.; Chai, W. J. Org. Chem. 1996, 61, 8598-8603. (b) Engler, T. A.; Chai, W.; LaTessa, K. O. J. Org. Chem. 1996, 61, 9297-9308.
36. 5 + 2 Cycloadducts are also found in reactions of quinone monoand bis-imides: (a) Engler, T. A.; Meduna, S. P.; LaTessa, K. O.; Chai, W. J. Org. Chem. 1996, 61, 8598-8603. (b) Engler, T. A.; Chai, W.; LaTessa, K. O. J. Org. Chem. 1996, 61, 9297-9308.
37. For 5 + 2 cycloadditions of carbocations formed in quinone monoketal solvolysis or phenol oxidation, see (a) Büchi, G.; Mak, C.-P. J. Am. Chem. Soc. 1977, 99, 8073-8075. (b) Büchi, G.; Chu, P.-S. J. Org. Chem. 1978, 43, 3717-3719. Mak, C.-P.; Büchi, G. J. Org. Chem. 1981, 46, 1-3. Mortlock, S. V.; Seckington, J. K.; Thomas, E. J. J. Chem. Soc., Perkin Trans 1 1988, 2305-2307. (e) Angle, S. R.; Turnbull, K. D. J. Org. Chem. 1993, 58, 5360-5369. Gates, B. D.; Dalidowicz, P.; Tebben, A.; Wang, S.; Swenton, J. S. J. Org. Chem. 1992, 57, 2135-2143. (g) Yamamura, S.; Shizuri, Y.; Shigemori, H.; Okuno, Y.; Ohkubo, M. Tetrahedron 1991, 47, 635-644. (h) Grieco, P. A.; Walker, J. K. Tetrahedron 1997, 53, 8975-8996. Collins, J. L.; Grieco, P. A., Walker, J. K. Tetrahedron Lett. 1997, 38, 1321-1324. An analogous process is the perezone to pipitzol rearrangement, see (j) Joseph-Nathan, P.; Santillan, R. L. In Studies in Natrural Product Chemistry; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam; 1989; Vol. 5, pp 763-813.
38. For 5 + 2 cycloadditions of carbocations formed in quinone monoketal solvolysis or phenol oxidation, see (a) Büchi, G.; Mak, C.-P. J. Am. Chem. Soc. 1977, 99, 8073-8075. (b) Büchi, G.; Chu, P.-S. J. Org. Chem. 1978, 43, 3717-3719. Mak, C.-P.; Büchi, G. J. Org. Chem. 1981, 46, 1-3. Mortlock, S. V.; Seckington, J. K.; Thomas, E. J. J. Chem. Soc., Perkin Trans 1 1988, 2305-2307. (e) Angle, S. R.; Turnbull, K. D. J. Org. Chem. 1993, 58, 5360-5369. Gates, B. D.; Dalidowicz, P.; Tebben, A.; Wang, S.; Swenton, J. S. J. Org. Chem. 1992, 57, 2135-2143. (g) Yamamura, S.; Shizuri, Y.; Shigemori, H.; Okuno, Y.; Ohkubo, M. Tetrahedron 1991, 47, 635-644. (h) Grieco, P. A.; Walker, J. K. Tetrahedron 1997, 53, 8975-8996. Collins, J. L.; Grieco, P. A., Walker, J. K. Tetrahedron Lett. 1997, 38, 1321-1324. An analogous process is the perezone to pipitzol rearrangement, see (j) Joseph-Nathan, P.; Santillan, R. L. In Studies in Natrural Product Chemistry; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam; 1989; Vol. 5, pp 763-813.
39. For 5 + 2 cycloadditions of carbocations formed in quinone monoketal solvolysis or phenol oxidation, see (a) Büchi, G.; Mak, C.-P. J. Am. Chem. Soc. 1977, 99, 8073-8075. (b) Büchi, G.; Chu, P.-S. J. Org. Chem. 1978, 43, 3717-3719. Mak, C.-P.; Büchi, G. J. Org. Chem. 1981, 46, 1-3. Mortlock, S. V.; Seckington, J. K.; Thomas, E. J. J. Chem. Soc., Perkin Trans 1 1988, 2305-2307. (e) Angle, S. R.; Turnbull, K. D. J. Org. Chem. 1993, 58, 5360-5369. Gates, B. D.; Dalidowicz, P.; Tebben, A.; Wang, S.; Swenton, J. S. J. Org. Chem. 1992, 57, 2135-2143. (g) Yamamura, S.; Shizuri, Y.; Shigemori, H.; Okuno, Y.; Ohkubo, M. Tetrahedron 1991, 47, 635-644. (h) Grieco, P. A.; Walker, J. K. Tetrahedron 1997, 53, 8975-8996. Collins, J. L.; Grieco, P. A., Walker, J. K. Tetrahedron Lett. 1997, 38, 1321-1324. An analogous process is the perezone to pipitzol rearrangement, see (j) Joseph-Nathan, P.; Santillan, R. L. In Studies in Natrural Product Chemistry; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam; 1989; Vol. 5, pp 763-813.
40. For 5 + 2 cycloadditions of carbocations formed in quinone monoketal solvolysis or phenol oxidation, see (a) Büchi, G.; Mak, C.-P. J. Am. Chem. Soc. 1977, 99, 8073-8075. (b) Büchi, G.; Chu, P.-S. J. Org. Chem. 1978, 43, 3717-3719. Mak, C.-P.; Büchi, G. J. Org. Chem. 1981, 46, 1-3. Mortlock, S. V.; Seckington, J. K.; Thomas, E. J. J. Chem. Soc., Perkin Trans 1 1988, 2305-2307. (e) Angle, S. R.; Turnbull, K. D. J. Org. Chem. 1993, 58, 5360-5369. Gates, B. D.; Dalidowicz, P.; Tebben, A.; Wang, S.; Swenton, J. S. J. Org. Chem. 1992, 57, 2135-2143. (g) Yamamura, S.; Shizuri, Y.; Shigemori, H.; Okuno, Y.; Ohkubo, M. Tetrahedron 1991, 47, 635-644. (h) Grieco, P. A.; Walker, J. K. Tetrahedron 1997, 53, 8975-8996. Collins, J. L.; Grieco, P. A., Walker, J. K. Tetrahedron Lett. 1997, 38, 1321-1324. An analogous process is the perezone to pipitzol rearrangement, see (j) Joseph-Nathan, P.; Santillan, R. L. In Studies in Natrural Product Chemistry; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam; 1989; Vol. 5, pp 763-813.
41. For 5 + 2 cycloadditions of carbocations formed in quinone monoketal solvolysis or phenol oxidation, see (a) Büchi, G.; Mak, C.-P. J. Am. Chem. Soc. 1977, 99, 8073-8075. (b) Büchi, G.; Chu, P.-S. J. Org. Chem. 1978, 43, 3717-3719. Mak, C.-P.; Büchi, G. J. Org. Chem. 1981, 46, 1-3. Mortlock, S. V.; Seckington, J. K.; Thomas, E. J. J. Chem. Soc., Perkin Trans 1 1988, 2305-2307. (e) Angle, S. R.; Turnbull, K. D. J. Org. Chem. 1993, 58, 5360-5369. Gates, B. D.; Dalidowicz, P.; Tebben, A.; Wang, S.; Swenton, J. S. J. Org. Chem. 1992, 57, 2135-2143. (g) Yamamura, S.; Shizuri, Y.; Shigemori, H.; Okuno, Y.; Ohkubo, M. Tetrahedron 1991, 47, 635-644. (h) Grieco, P. A.; Walker, J. K. Tetrahedron 1997, 53, 8975-8996. Collins, J. L.; Grieco, P. A., Walker, J. K. Tetrahedron Lett. 1997, 38, 1321-1324. An analogous process is the perezone to pipitzol rearrangement, see (j) Joseph-Nathan, P.; Santillan, R. L. In Studies in Natrural Product Chemistry; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam; 1989; Vol. 5, pp 763-813.
42. For 5 + 2 cycloadditions of carbocations formed in quinone monoketal solvolysis or phenol oxidation, see (a) Büchi, G.; Mak, C.-P. J. Am. Chem. Soc. 1977, 99, 8073-8075. (b) Büchi, G.; Chu, P.-S. J. Org. Chem. 1978, 43, 3717-3719. Mak, C.-P.; Büchi, G. J. Org. Chem. 1981, 46, 1-3. Mortlock, S. V.; Seckington, J. K.; Thomas, E. J. J. Chem. Soc., Perkin Trans 1 1988, 2305-2307. (e) Angle, S. R.; Turnbull, K. D. J. Org. Chem. 1993, 58, 5360-5369. Gates, B. D.; Dalidowicz, P.; Tebben, A.; Wang, S.; Swenton, J. S. J. Org. Chem. 1992, 57, 2135-2143. (g) Yamamura, S.; Shizuri, Y.; Shigemori, H.; Okuno, Y.; Ohkubo, M. Tetrahedron 1991, 47, 635-644. (h) Grieco, P. A.; Walker, J. K. Tetrahedron 1997, 53, 8975-8996. Collins, J. L.; Grieco, P. A., Walker, J. K. Tetrahedron Lett. 1997, 38, 1321-1324. An analogous process is the perezone to pipitzol rearrangement, see (j) Joseph-Nathan, P.; Santillan, R. L. In Studies in Natrural Product Chemistry; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam; 1989; Vol. 5, pp 763-813.
43. For 5 + 2 cycloadditions of carbocations formed in quinone monoketal solvolysis or phenol oxidation, see (a) Büchi, G.; Mak, C.-P. J. Am. Chem. Soc. 1977, 99, 8073-8075. (b) Büchi, G.; Chu, P.-S. J. Org. Chem. 1978, 43, 3717-3719. Mak, C.-P.; Büchi, G. J. Org. Chem. 1981, 46, 1-3. Mortlock, S. V.; Seckington, J. K.; Thomas, E. J. J. Chem. Soc., Perkin Trans 1 1988, 2305-2307. (e) Angle, S. R.; Turnbull, K. D. J. Org. Chem. 1993, 58, 5360-5369. Gates, B. D.; Dalidowicz, P.; Tebben, A.; Wang, S.; Swenton, J. S. J. Org. Chem. 1992, 57, 2135-2143. (g) Yamamura, S.; Shizuri, Y.; Shigemori, H.; Okuno, Y.; Ohkubo, M. Tetrahedron 1991, 47, 635-644. (h) Grieco, P. A.; Walker, J. K. Tetrahedron 1997, 53, 8975-8996. Collins, J. L.; Grieco, P. A., Walker, J. K. Tetrahedron Lett. 1997, 38, 1321-1324. An analogous process is the perezone to pipitzol rearrangement, see (j) Joseph-Nathan, P.; Santillan, R. L. In Studies in Natrural Product Chemistry; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam; 1989; Vol. 5, pp 763-813.
44. For 5 + 2 cycloadditions of carbocations formed in quinone monoketal solvolysis or phenol oxidation, see (a) Büchi, G.; Mak, C.-P. J. Am. Chem. Soc. 1977, 99, 8073-8075. (b) Büchi, G.; Chu, P.-S. J. Org. Chem. 1978, 43, 3717-3719. Mak, C.-P.; Büchi, G. J. Org. Chem. 1981, 46, 1-3. Mortlock, S. V.; Seckington, J. K.; Thomas, E. J. J. Chem. Soc., Perkin Trans 1 1988, 2305-2307. (e) Angle, S. R.; Turnbull, K. D. J. Org. Chem. 1993, 58, 5360-5369. Gates, B. D.; Dalidowicz, P.; Tebben, A.; Wang, S.; Swenton, J. S. J. Org. Chem. 1992, 57, 2135-2143. (g) Yamamura, S.; Shizuri, Y.; Shigemori, H.; Okuno, Y.; Ohkubo, M. Tetrahedron 1991, 47, 635-644. (h) Grieco, P. A.; Walker, J. K. Tetrahedron 1997, 53, 8975-8996. Collins, J. L.; Grieco, P. A., Walker, J. K. Tetrahedron Lett. 1997, 38, 1321-1324. An analogous process is the perezone to pipitzol rearrangement, see (j) Joseph-Nathan, P.; Santillan, R. L. In Studies in Natrural Product Chemistry; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam; 1989; Vol. 5, pp 763-813.
45. For 5 + 2 cycloadditions of carbocations formed in quinone monoketal solvolysis or phenol oxidation, see (a) Büchi, G.; Mak, C.-P. J. Am. Chem. Soc. 1977, 99, 8073-8075. (b) Büchi, G.; Chu, P.-S. J. Org. Chem. 1978, 43, 3717-3719. Mak, C.-P.; Büchi, G. J. Org. Chem. 1981, 46, 1-3. Mortlock, S. V.; Seckington, J. K.; Thomas, E. J. J. Chem. Soc., Perkin Trans 1 1988, 2305-2307. (e) Angle, S. R.; Turnbull, K. D. J. Org. Chem. 1993, 58, 5360-5369. Gates, B. D.; Dalidowicz, P.; Tebben, A.; Wang, S.; Swenton, J. S. J. Org. Chem. 1992, 57, 2135-2143. (g) Yamamura, S.; Shizuri, Y.; Shigemori, H.; Okuno, Y.; Ohkubo, M. Tetrahedron 1991, 47, 635-644. (h) Grieco, P. A.; Walker, J. K. Tetrahedron 1997, 53, 8975-8996. Collins, J. L.; Grieco, P. A., Walker, J. K. Tetrahedron Lett. 1997, 38, 1321-1324. An analogous process is the perezone to pipitzol rearrangement, see (j) Joseph-Nathan, P.; Santillan, R. L. In Studies in Natrural Product Chemistry; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam; 1989; Vol. 5, pp 763-813.
46. For 5 + 2 cycloadditions of carbocations formed in quinone monoketal solvolysis or phenol oxidation, see (a) Büchi, G.; Mak, C.-P. J. Am. Chem. Soc. 1977, 99, 8073-8075. (b) Büchi, G.; Chu, P.-S. J. Org. Chem. 1978, 43, 3717-3719. Mak, C.-P.; Büchi, G. J. Org. Chem. 1981, 46, 1-3. Mortlock, S. V.; Seckington, J. K.; Thomas, E. J. J. Chem. Soc., Perkin Trans 1 1988, 2305-2307. (e) Angle, S. R.; Turnbull, K. D. J. Org. Chem. 1993, 58, 5360-5369. Gates, B. D.; Dalidowicz, P.; Tebben, A.; Wang, S.; Swenton, J. S. J. Org. Chem. 1992, 57, 2135-2143. (g) Yamamura, S.; Shizuri, Y.; Shigemori, H.; Okuno, Y.; Ohkubo, M. Tetrahedron 1991, 47, 635-644. (h) Grieco, P. A.; Walker, J. K. Tetrahedron 1997, 53, 8975-8996. Collins, J. L.; Grieco, P. A., Walker, J. K. Tetrahedron Lett. 1997, 38, 1321-1324. An analogous process is the perezone to pipitzol rearrangement, see (j) Joseph-Nathan, P.; Santillan, R. L. In Studies in Natrural Product Chemistry; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam; 1989; Vol. 5, pp 763-813.
47. 3,4
48. Intramolecular carbocation activation of quinones to intermolecular cycloaddition has been reported; e.g. i to ii, see Mamont, P. Bull. Soc. Chim. Fr. 1970, 1557-1564.
49. 1H NOE, COSY, HMQC, and HMBC spectra and a discussion of this structure assignment are included in the Supporting Information.
50. 3a For reports of Ti(IV)-oxidation of electron-rich alkenes, see (a) Inaba, S.-i.; Ojima, I. Tetrahedron Lett. 1977, 2009-2012. (b) Reetz, M. T.; Schwellnus, K.; Hubner, F.; Massa, W.; Schmidt, R. E. Chem. Ber. 1983, 116, 3708-3724. Jacobsen, E. J.; Totten, G. E.; Wenke, G.; Karydas, A. C.; Knodes, Y. E. Synth. Commun. 1985, 15, 301-306.
51. 3a For reports of Ti(IV)-oxidation of electron-rich alkenes, see (a) Inaba, S.-i.; Ojima, I. Tetrahedron Lett. 1977, 2009-2012. (b) Reetz, M. T.; Schwellnus, K.; Hubner, F.; Massa, W.; Schmidt, R. E. Chem. Ber. 1983, 116, 3708-3724. Jacobsen, E. J.; Totten, G. E.; Wenke, G.; Karydas, A. C.; Knodes, Y. E. Synth. Commun. 1985, 15, 301-306.
52. 3a For reports of Ti(IV)-oxidation of electron-rich alkenes, see (a) Inaba, S.-i.; Ojima, I. Tetrahedron Lett. 1977, 2009-2012. (b) Reetz, M. T.; Schwellnus, K.; Hubner, F.; Massa, W.; Schmidt, R. E. Chem. Ber. 1983, 116, 3708-3724. Jacobsen, E. J.; Totten, G. E.; Wenke, G.; Karydas, A. C.; Knodes, Y. E. Synth. Commun. 1985, 15, 301-306.
53. The authors have deposited atomic coordinates for structures 7a, 9, 11, 14, and 16 with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, CB2 1EZ, U.K.