Iodine atom transfer [3 + 2] cycloaddition reaction with electron-rich alkenes using N-tosyliodoaziridine derivatives as novel azahomoallyl radical precursors

Journal of Organic Chemistry

Volumn 68, Issue 8, 2003, Pages 3184-3189

  Kitagawa, Osamu ^a   Miyaji, Shinsaku ^a   Yamada, Yoichiro ^a   Fujiwara, Hiroki ^a   Taguchi, Takeo ^a  

^a TOKYO UNIVERSITY OF PHARMACY AND LIFE SCIENCES   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOADDITION REACTIONS;

ADDITION REACTIONS; DERIVATIVES; ETHERS; IODINE; OLEFINS;

NITROGEN COMPOUNDS;

ACETAL DERIVATIVE; ALKENE DERIVATIVE; ALLYL COMPOUND; AZIRIDINE DERIVATIVE; BICYCLO COMPOUND; ETHER DERIVATIVE; HEPTANE; INDOLE DERIVATIVE; IODINE; KETENE DERIVATIVE; PYRROLIDINE DERIVATIVE; RADICAL; TOLUENESULFONIC ACID DERIVATIVE;

ARTICLE; ATOM; CHEMICAL BOND; CYCLOADDITION; ELECTRON; OPTICAL ROTATION; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0037453567     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0266846     Document Type: Article

References (56)

1. The reaction with electron-deficient alkenes: (a) Clieve, D. L. J.; Angoh, A. G. J. Chem. Soc., Chem. Commun. 1985, 980-982. (b) Cekovik, Z.; Saicic, R. Tetrahedron Lett. 1986, 27, 5893-5896. (c) Curran, D. P.; Chen, M. J. Am. Chem. Soc. 1987, 109, 6558-6560. (d) Barton, D. H. R.; Zard, S. Z.; daSilva, E. J. Chem. Soc., Chem. Commun. 1988, 285-287. (e) Feldman, K. S.; Romanelli, A. L.; Ruckle, R. E., Jr.; Miller, R. F. J. Am. Chem. Soc. 1988, 110, 3300-3302. (f) Curran, D. P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I. Eds.; Pergamon Press: New York, 1991; Vol. 4, pp 779-831 and references therein. The reaction with simple alkenes: (g) Miura, K.; Fugami, K.; Ohshima, K.; Utimoto, K. Tetrahedron Lett. 1988, 29, 5135-5138. (h) Curran, D. P.; Chen, M.; Spletzer, E. J. Am. Chem. Soc. 1989, 111, 8872-8878. (i) Chuang, C. P.; Hou, S. S.; Ngoi, T. H. J. J. Chem. Res., Synop. 1991, 216-217. (j) Curran, D. P.; Seong, C. M. Tetrahedron 1992, 48, 2157-2174. (k) Curran, D. P.; Seong, C. M. Tetrahedron 1992, 48, 2175-2190. (l) Maslak, V.; Cekovic, Z.; Saicic, R. N. Synlett 1998, 1435-1437. (m) McCarroll, A. J.; Walton, J. C. J. Chem. Soc., Perkin Trans. 1 2001, 3215-3229. (n) Kitagawa, O.; Fujiwara, H.; Taguchi, T. Tetrahedron Lett. 2001, 42, 2165-2167. (o) Kitagawa, O.; Yamada, Y.; Fujiwara, H.;. Taguchi, T. J. Org. Chem. 2002, 67, 922-927. (p) Kitagawa, O.; Yamada, Y.; Sugawara, A.; Taguchi, T. Org. Lett. 2002, 4, 1011-1013.
2. The reaction with electron-deficient alkenes: (a) Clieve, D. L. J.; Angoh, A. G. J. Chem. Soc., Chem. Commun. 1985, 980-982. (b) Cekovik, Z.; Saicic, R. Tetrahedron Lett. 1986, 27, 5893-5896. (c) Curran, D. P.; Chen, M. J. Am. Chem. Soc. 1987, 109, 6558-6560. (d) Barton, D. H. R.; Zard, S. Z.; daSilva, E. J. Chem. Soc., Chem. Commun. 1988, 285-287. (e) Feldman, K. S.; Romanelli, A. L.; Ruckle, R. E., Jr.; Miller, R. F. J. Am. Chem. Soc. 1988, 110, 3300-3302. (f) Curran, D. P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I. Eds.; Pergamon Press: New York, 1991; Vol. 4, pp 779-831 and references therein. The reaction with simple alkenes: (g) Miura, K.; Fugami, K.; Ohshima, K.; Utimoto, K. Tetrahedron Lett. 1988, 29, 5135-5138. (h) Curran, D. P.; Chen, M.; Spletzer, E. J. Am. Chem. Soc. 1989, 111, 8872-8878. (i) Chuang, C. P.; Hou, S. S.; Ngoi, T. H. J. J. Chem. Res., Synop. 1991, 216-217. (j) Curran, D. P.; Seong, C. M. Tetrahedron 1992, 48, 2157-2174. (k) Curran, D. P.; Seong, C. M. Tetrahedron 1992, 48, 2175-2190. (l) Maslak, V.; Cekovic, Z.; Saicic, R. N. Synlett 1998, 1435-1437. (m) McCarroll, A. J.; Walton, J. C. J. Chem. Soc., Perkin Trans. 1 2001, 3215-3229. (n) Kitagawa, O.; Fujiwara, H.; Taguchi, T. Tetrahedron Lett. 2001, 42, 2165-2167. (o) Kitagawa, O.; Yamada, Y.; Fujiwara, H.;. Taguchi, T. J. Org. Chem. 2002, 67, 922-927. (p) Kitagawa, O.; Yamada, Y.; Sugawara, A.; Taguchi, T. Org. Lett. 2002, 4, 1011-1013.
3. The reaction with electron-deficient alkenes: (a) Clieve, D. L. J.; Angoh, A. G. J. Chem. Soc., Chem. Commun. 1985, 980-982. (b) Cekovik, Z.; Saicic, R. Tetrahedron Lett. 1986, 27, 5893-5896. (c) Curran, D. P.; Chen, M. J. Am. Chem. Soc. 1987, 109, 6558-6560. (d) Barton, D. H. R.; Zard, S. Z.; daSilva, E. J. Chem. Soc., Chem. Commun. 1988, 285-287. (e) Feldman, K. S.; Romanelli, A. L.; Ruckle, R. E., Jr.; Miller, R. F. J. Am. Chem. Soc. 1988, 110, 3300-3302. (f) Curran, D. P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I. Eds.; Pergamon Press: New York, 1991; Vol. 4, pp 779-831 and references therein. The reaction with simple alkenes: (g) Miura, K.; Fugami, K.; Ohshima, K.; Utimoto, K. Tetrahedron Lett. 1988, 29, 5135-5138. (h) Curran, D. P.; Chen, M.; Spletzer, E. J. Am. Chem. Soc. 1989, 111, 8872-8878. (i) Chuang, C. P.; Hou, S. S.; Ngoi, T. H. J. J. Chem. Res., Synop. 1991, 216-217. (j) Curran, D. P.; Seong, C. M. Tetrahedron 1992, 48, 2157-2174. (k) Curran, D. P.; Seong, C. M. Tetrahedron 1992, 48, 2175-2190. (l) Maslak, V.; Cekovic, Z.; Saicic, R. N. Synlett 1998, 1435-1437. (m) McCarroll, A. J.; Walton, J. C. J. Chem. Soc., Perkin Trans. 1 2001, 3215-3229. (n) Kitagawa, O.; Fujiwara, H.; Taguchi, T. Tetrahedron Lett. 2001, 42, 2165-2167. (o) Kitagawa, O.; Yamada, Y.; Fujiwara, H.;. Taguchi, T. J. Org. Chem. 2002, 67, 922-927. (p) Kitagawa, O.; Yamada, Y.; Sugawara, A.; Taguchi, T. Org. Lett. 2002, 4, 1011-1013.
4. The reaction with electron-deficient alkenes: (a) Clieve, D. L. J.; Angoh, A. G. J. Chem. Soc., Chem. Commun. 1985, 980-982. (b) Cekovik, Z.; Saicic, R. Tetrahedron Lett. 1986, 27, 5893-5896. (c) Curran, D. P.; Chen, M. J. Am. Chem. Soc. 1987, 109, 6558-6560. (d) Barton, D. H. R.; Zard, S. Z.; daSilva, E. J. Chem. Soc., Chem. Commun. 1988, 285-287. (e) Feldman, K. S.; Romanelli, A. L.; Ruckle, R. E., Jr.; Miller, R. F. J. Am. Chem. Soc. 1988, 110, 3300-3302. (f) Curran, D. P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I. Eds.; Pergamon Press: New York, 1991; Vol. 4, pp 779-831 and references therein. The reaction with simple alkenes: (g) Miura, K.; Fugami, K.; Ohshima, K.; Utimoto, K. Tetrahedron Lett. 1988, 29, 5135-5138. (h) Curran, D. P.; Chen, M.; Spletzer, E. J. Am. Chem. Soc. 1989, 111, 8872-8878. (i) Chuang, C. P.; Hou, S. S.; Ngoi, T. H. J. J. Chem. Res., Synop. 1991, 216-217. (j) Curran, D. P.; Seong, C. M. Tetrahedron 1992, 48, 2157-2174. (k) Curran, D. P.; Seong, C. M. Tetrahedron 1992, 48, 2175-2190. (l) Maslak, V.; Cekovic, Z.; Saicic, R. N. Synlett 1998, 1435-1437. (m) McCarroll, A. J.; Walton, J. C. J. Chem. Soc., Perkin Trans. 1 2001, 3215-3229. (n) Kitagawa, O.; Fujiwara, H.; Taguchi, T. Tetrahedron Lett. 2001, 42, 2165-2167. (o) Kitagawa, O.; Yamada, Y.; Fujiwara, H.;. Taguchi, T. J. Org. Chem. 2002, 67, 922-927. (p) Kitagawa, O.; Yamada, Y.; Sugawara, A.; Taguchi, T. Org. Lett. 2002, 4, 1011-1013.
5. The reaction with electron-deficient alkenes: (a) Clieve, D. L. J.; Angoh, A. G. J. Chem. Soc., Chem. Commun. 1985, 980-982. (b) Cekovik, Z.; Saicic, R. Tetrahedron Lett. 1986, 27, 5893-5896. (c) Curran, D. P.; Chen, M. J. Am. Chem. Soc. 1987, 109, 6558-6560. (d) Barton, D. H. R.; Zard, S. Z.; daSilva, E. J. Chem. Soc., Chem. Commun. 1988, 285-287. (e) Feldman, K. S.; Romanelli, A. L.; Ruckle, R. E., Jr.; Miller, R. F. J. Am. Chem. Soc. 1988, 110, 3300-3302. (f) Curran, D. P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I. Eds.; Pergamon Press: New York, 1991; Vol. 4, pp 779-831 and references therein. The reaction with simple alkenes: (g) Miura, K.; Fugami, K.; Ohshima, K.; Utimoto, K. Tetrahedron Lett. 1988, 29, 5135-5138. (h) Curran, D. P.; Chen, M.; Spletzer, E. J. Am. Chem. Soc. 1989, 111, 8872-8878. (i) Chuang, C. P.; Hou, S. S.; Ngoi, T. H. J. J. Chem. Res., Synop. 1991, 216-217. (j) Curran, D. P.; Seong, C. M. Tetrahedron 1992, 48, 2157-2174. (k) Curran, D. P.; Seong, C. M. Tetrahedron 1992, 48, 2175-2190. (l) Maslak, V.; Cekovic, Z.; Saicic, R. N. Synlett 1998, 1435-1437. (m) McCarroll, A. J.; Walton, J. C. J. Chem. Soc., Perkin Trans. 1 2001, 3215-3229. (n) Kitagawa, O.; Fujiwara, H.; Taguchi, T. Tetrahedron Lett. 2001, 42, 2165-2167. (o) Kitagawa, O.; Yamada, Y.; Fujiwara, H.;. Taguchi, T. J. Org. Chem. 2002, 67, 922-927. (p) Kitagawa, O.; Yamada, Y.; Sugawara, A.; Taguchi, T. Org. Lett. 2002, 4, 1011-1013.
6. The reaction with electron-deficient alkenes: (a) Clieve, D. L. J.; Angoh, A. G. J. Chem. Soc., Chem. Commun. 1985, 980-982. (b) Cekovik, Z.; Saicic, R. Tetrahedron Lett. 1986, 27, 5893-5896. (c) Curran, D. P.; Chen, M. J. Am. Chem. Soc. 1987, 109, 6558-6560. (d) Barton, D. H. R.; Zard, S. Z.; daSilva, E. J. Chem. Soc., Chem. Commun. 1988, 285-287. (e) Feldman, K. S.; Romanelli, A. L.; Ruckle, R. E., Jr.; Miller, R. F. J. Am. Chem. Soc. 1988, 110, 3300-3302. (f) Curran, D. P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I. Eds.; Pergamon Press: New York, 1991; Vol. 4, pp 779-831 and references therein. The reaction with simple alkenes: (g) Miura, K.; Fugami, K.; Ohshima, K.; Utimoto, K. Tetrahedron Lett. 1988, 29, 5135-5138. (h) Curran, D. P.; Chen, M.; Spletzer, E. J. Am. Chem. Soc. 1989, 111, 8872-8878. (i) Chuang, C. P.; Hou, S. S.; Ngoi, T. H. J. J. Chem. Res., Synop. 1991, 216-217. (j) Curran, D. P.; Seong, C. M. Tetrahedron 1992, 48, 2157-2174. (k) Curran, D. P.; Seong, C. M. Tetrahedron 1992, 48, 2175-2190. (l) Maslak, V.; Cekovic, Z.; Saicic, R. N. Synlett 1998, 1435-1437. (m) McCarroll, A. J.; Walton, J. C. J. Chem. Soc., Perkin Trans. 1 2001, 3215-3229. (n) Kitagawa, O.; Fujiwara, H.; Taguchi, T. Tetrahedron Lett. 2001, 42, 2165-2167. (o) Kitagawa, O.; Yamada, Y.; Fujiwara, H.;. Taguchi, T. J. Org. Chem. 2002, 67, 922-927. (p) Kitagawa, O.; Yamada, Y.; Sugawara, A.; Taguchi, T. Org. Lett. 2002, 4, 1011-1013.
7. The reaction with electron-deficient alkenes: (a) Clieve, D. L. J.; Angoh, A. G. J. Chem. Soc., Chem. Commun. 1985, 980-982. (b) Cekovik, Z.; Saicic, R. Tetrahedron Lett. 1986, 27, 5893-5896. (c) Curran, D. P.; Chen, M. J. Am. Chem. Soc. 1987, 109, 6558-6560. (d) Barton, D. H. R.; Zard, S. Z.; daSilva, E. J. Chem. Soc., Chem. Commun. 1988, 285-287. (e) Feldman, K. S.; Romanelli, A. L.; Ruckle, R. E., Jr.; Miller, R. F. J. Am. Chem. Soc. 1988, 110, 3300-3302. (f) Curran, D. P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I. Eds.; Pergamon Press: New York, 1991; Vol. 4, pp 779-831 and references therein. The reaction with simple alkenes: (g) Miura, K.; Fugami, K.; Ohshima, K.; Utimoto, K. Tetrahedron Lett. 1988, 29, 5135-5138. (h) Curran, D. P.; Chen, M.; Spletzer, E. J. Am. Chem. Soc. 1989, 111, 8872-8878. (i) Chuang, C. P.; Hou, S. S.; Ngoi, T. H. J. J. Chem. Res., Synop. 1991, 216-217. (j) Curran, D. P.; Seong, C. M. Tetrahedron 1992, 48, 2157-2174. (k) Curran, D. P.; Seong, C. M. Tetrahedron 1992, 48, 2175-2190. (l) Maslak, V.; Cekovic, Z.; Saicic, R. N. Synlett 1998, 1435-1437. (m) McCarroll, A. J.; Walton, J. C. J. Chem. Soc., Perkin Trans. 1 2001, 3215-3229. (n) Kitagawa, O.; Fujiwara, H.; Taguchi, T. Tetrahedron Lett. 2001, 42, 2165-2167. (o) Kitagawa, O.; Yamada, Y.; Fujiwara, H.;. Taguchi, T. J. Org. Chem. 2002, 67, 922-927. (p) Kitagawa, O.; Yamada, Y.; Sugawara, A.; Taguchi, T. Org. Lett. 2002, 4, 1011-1013.
8. The reaction with electron-deficient alkenes: (a) Clieve, D. L. J.; Angoh, A. G. J. Chem. Soc., Chem. Commun. 1985, 980-982. (b) Cekovik, Z.; Saicic, R. Tetrahedron Lett. 1986, 27, 5893-5896. (c) Curran, D. P.; Chen, M. J. Am. Chem. Soc. 1987, 109, 6558-6560. (d) Barton, D. H. R.; Zard, S. Z.; daSilva, E. J. Chem. Soc., Chem. Commun. 1988, 285-287. (e) Feldman, K. S.; Romanelli, A. L.; Ruckle, R. E., Jr.; Miller, R. F. J. Am. Chem. Soc. 1988, 110, 3300-3302. (f) Curran, D. P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I. Eds.; Pergamon Press: New York, 1991; Vol. 4, pp 779-831 and references therein. The reaction with simple alkenes: (g) Miura, K.; Fugami, K.; Ohshima, K.; Utimoto, K. Tetrahedron Lett. 1988, 29, 5135-5138. (h) Curran, D. P.; Chen, M.; Spletzer, E. J. Am. Chem. Soc. 1989, 111, 8872-8878. (i) Chuang, C. P.; Hou, S. S.; Ngoi, T. H. J. J. Chem. Res., Synop. 1991, 216-217. (j) Curran, D. P.; Seong, C. M. Tetrahedron 1992, 48, 2157-2174. (k) Curran, D. P.; Seong, C. M. Tetrahedron 1992, 48, 2175-2190. (l) Maslak, V.; Cekovic, Z.; Saicic, R. N. Synlett 1998, 1435-1437. (m) McCarroll, A. J.; Walton, J. C. J. Chem. Soc., Perkin Trans. 1 2001, 3215-3229. (n) Kitagawa, O.; Fujiwara, H.; Taguchi, T. Tetrahedron Lett. 2001, 42, 2165-2167. (o) Kitagawa, O.; Yamada, Y.; Fujiwara, H.;. Taguchi, T. J. Org. Chem. 2002, 67, 922-927. (p) Kitagawa, O.; Yamada, Y.; Sugawara, A.; Taguchi, T. Org. Lett. 2002, 4, 1011-1013.
9. The reaction with electron-deficient alkenes: (a) Clieve, D. L. J.; Angoh, A. G. J. Chem. Soc., Chem. Commun. 1985, 980-982. (b) Cekovik, Z.; Saicic, R. Tetrahedron Lett. 1986, 27, 5893-5896. (c) Curran, D. P.; Chen, M. J. Am. Chem. Soc. 1987, 109, 6558-6560. (d) Barton, D. H. R.; Zard, S. Z.; daSilva, E. J. Chem. Soc., Chem. Commun. 1988, 285-287. (e) Feldman, K. S.; Romanelli, A. L.; Ruckle, R. E., Jr.; Miller, R. F. J. Am. Chem. Soc. 1988, 110, 3300-3302. (f) Curran, D. P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I. Eds.; Pergamon Press: New York, 1991; Vol. 4, pp 779-831 and references therein. The reaction with simple alkenes: (g) Miura, K.; Fugami, K.; Ohshima, K.; Utimoto, K. Tetrahedron Lett. 1988, 29, 5135-5138. (h) Curran, D. P.; Chen, M.; Spletzer, E. J. Am. Chem. Soc. 1989, 111, 8872-8878. (i) Chuang, C. P.; Hou, S. S.; Ngoi, T. H. J. J. Chem. Res., Synop. 1991, 216-217. (j) Curran, D. P.; Seong, C. M. Tetrahedron 1992, 48, 2157-2174. (k) Curran, D. P.; Seong, C. M. Tetrahedron 1992, 48, 2175-2190. (l) Maslak, V.; Cekovic, Z.; Saicic, R. N. Synlett 1998, 1435-1437. (m) McCarroll, A. J.; Walton, J. C. J. Chem. Soc., Perkin Trans. 1 2001, 3215-3229. (n) Kitagawa, O.; Fujiwara, H.; Taguchi, T. Tetrahedron Lett. 2001, 42, 2165-2167. (o) Kitagawa, O.; Yamada, Y.; Fujiwara, H.;. Taguchi, T. J. Org. Chem. 2002, 67, 922-927. (p) Kitagawa, O.; Yamada, Y.; Sugawara, A.; Taguchi, T. Org. Lett. 2002, 4, 1011-1013.
10. The reaction with electron-deficient alkenes: (a) Clieve, D. L. J.; Angoh, A. G. J. Chem. Soc., Chem. Commun. 1985, 980-982. (b) Cekovik, Z.; Saicic, R. Tetrahedron Lett. 1986, 27, 5893-5896. (c) Curran, D. P.; Chen, M. J. Am. Chem. Soc. 1987, 109, 6558-6560. (d) Barton, D. H. R.; Zard, S. Z.; daSilva, E. J. Chem. Soc., Chem. Commun. 1988, 285-287. (e) Feldman, K. S.; Romanelli, A. L.; Ruckle, R. E., Jr.; Miller, R. F. J. Am. Chem. Soc. 1988, 110, 3300-3302. (f) Curran, D. P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I. Eds.; Pergamon Press: New York, 1991; Vol. 4, pp 779-831 and references therein. The reaction with simple alkenes: (g) Miura, K.; Fugami, K.; Ohshima, K.; Utimoto, K. Tetrahedron Lett. 1988, 29, 5135-5138. (h) Curran, D. P.; Chen, M.; Spletzer, E. J. Am. Chem. Soc. 1989, 111, 8872-8878. (i) Chuang, C. P.; Hou, S. S.; Ngoi, T. H. J. J. Chem. Res., Synop. 1991, 216-217. (j) Curran, D. P.; Seong, C. M. Tetrahedron 1992, 48, 2157-2174. (k) Curran, D. P.; Seong, C. M. Tetrahedron 1992, 48, 2175-2190. (l) Maslak, V.; Cekovic, Z.; Saicic, R. N. Synlett 1998, 1435-1437. (m) McCarroll, A. J.; Walton, J. C. J. Chem. Soc., Perkin Trans. 1 2001, 3215-3229. (n) Kitagawa, O.; Fujiwara, H.; Taguchi, T. Tetrahedron Lett. 2001, 42, 2165-2167. (o) Kitagawa, O.; Yamada, Y.; Fujiwara, H.;. Taguchi, T. J. Org. Chem. 2002, 67, 922-927. (p) Kitagawa, O.; Yamada, Y.; Sugawara, A.; Taguchi, T. Org. Lett. 2002, 4, 1011-1013.
11. The reaction with electron-deficient alkenes: (a) Clieve, D. L. J.; Angoh, A. G. J. Chem. Soc., Chem. Commun. 1985, 980-982. (b) Cekovik, Z.; Saicic, R. Tetrahedron Lett. 1986, 27, 5893-5896. (c) Curran, D. P.; Chen, M. J. Am. Chem. Soc. 1987, 109, 6558-6560. (d) Barton, D. H. R.; Zard, S. Z.; daSilva, E. J. Chem. Soc., Chem. Commun. 1988, 285-287. (e) Feldman, K. S.; Romanelli, A. L.; Ruckle, R. E., Jr.; Miller, R. F. J. Am. Chem. Soc. 1988, 110, 3300-3302. (f) Curran, D. P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I. Eds.; Pergamon Press: New York, 1991; Vol. 4, pp 779-831 and references therein. The reaction with simple alkenes: (g) Miura, K.; Fugami, K.; Ohshima, K.; Utimoto, K. Tetrahedron Lett. 1988, 29, 5135-5138. (h) Curran, D. P.; Chen, M.; Spletzer, E. J. Am. Chem. Soc. 1989, 111, 8872-8878. (i) Chuang, C. P.; Hou, S. S.; Ngoi, T. H. J. J. Chem. Res., Synop. 1991, 216-217. (j) Curran, D. P.; Seong, C. M. Tetrahedron 1992, 48, 2157-2174. (k) Curran, D. P.; Seong, C. M. Tetrahedron 1992, 48, 2175-2190. (l) Maslak, V.; Cekovic, Z.; Saicic, R. N. Synlett 1998, 1435-1437. (m) McCarroll, A. J.; Walton, J. C. J. Chem. Soc., Perkin Trans. 1 2001, 3215-3229. (n) Kitagawa, O.; Fujiwara, H.; Taguchi, T. Tetrahedron Lett. 2001, 42, 2165-2167. (o) Kitagawa, O.; Yamada, Y.; Fujiwara, H.;. Taguchi, T. J. Org. Chem. 2002, 67, 922-927. (p) Kitagawa, O.; Yamada, Y.; Sugawara, A.; Taguchi, T. Org. Lett. 2002, 4, 1011-1013.
12. The reaction with electron-deficient alkenes: (a) Clieve, D. L. J.; Angoh, A. G. J. Chem. Soc., Chem. Commun. 1985, 980-982. (b) Cekovik, Z.; Saicic, R. Tetrahedron Lett. 1986, 27, 5893-5896. (c) Curran, D. P.; Chen, M. J. Am. Chem. Soc. 1987, 109, 6558-6560. (d) Barton, D. H. R.; Zard, S. Z.; daSilva, E. J. Chem. Soc., Chem. Commun. 1988, 285-287. (e) Feldman, K. S.; Romanelli, A. L.; Ruckle, R. E., Jr.; Miller, R. F. J. Am. Chem. Soc. 1988, 110, 3300-3302. (f) Curran, D. P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I. Eds.; Pergamon Press: New York, 1991; Vol. 4, pp 779-831 and references therein. The reaction with simple alkenes: (g) Miura, K.; Fugami, K.; Ohshima, K.; Utimoto, K. Tetrahedron Lett. 1988, 29, 5135-5138. (h) Curran, D. P.; Chen, M.; Spletzer, E. J. Am. Chem. Soc. 1989, 111, 8872-8878. (i) Chuang, C. P.; Hou, S. S.; Ngoi, T. H. J. J. Chem. Res., Synop. 1991, 216-217. (j) Curran, D. P.; Seong, C. M. Tetrahedron 1992, 48, 2157-2174. (k) Curran, D. P.; Seong, C. M. Tetrahedron 1992, 48, 2175-2190. (l) Maslak, V.; Cekovic, Z.; Saicic, R. N. Synlett 1998, 1435-1437. (m) McCarroll, A. J.; Walton, J. C. J. Chem. Soc., Perkin Trans. 1 2001, 3215-3229. (n) Kitagawa, O.; Fujiwara, H.; Taguchi, T. Tetrahedron Lett. 2001, 42, 2165-2167. (o) Kitagawa, O.; Yamada, Y.; Fujiwara, H.;. Taguchi, T. J. Org. Chem. 2002, 67, 922-927. (p) Kitagawa, O.; Yamada, Y.; Sugawara, A.; Taguchi, T. Org. Lett. 2002, 4, 1011-1013.
13. The reaction with electron-deficient alkenes: (a) Clieve, D. L. J.; Angoh, A. G. J. Chem. Soc., Chem. Commun. 1985, 980-982. (b) Cekovik, Z.; Saicic, R. Tetrahedron Lett. 1986, 27, 5893-5896. (c) Curran, D. P.; Chen, M. J. Am. Chem. Soc. 1987, 109, 6558-6560. (d) Barton, D. H. R.; Zard, S. Z.; daSilva, E. J. Chem. Soc., Chem. Commun. 1988, 285-287. (e) Feldman, K. S.; Romanelli, A. L.; Ruckle, R. E., Jr.; Miller, R. F. J. Am. Chem. Soc. 1988, 110, 3300-3302. (f) Curran, D. P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I. Eds.; Pergamon Press: New York, 1991; Vol. 4, pp 779-831 and references therein. The reaction with simple alkenes: (g) Miura, K.; Fugami, K.; Ohshima, K.; Utimoto, K. Tetrahedron Lett. 1988, 29, 5135-5138. (h) Curran, D. P.; Chen, M.; Spletzer, E. J. Am. Chem. Soc. 1989, 111, 8872-8878. (i) Chuang, C. P.; Hou, S. S.; Ngoi, T. H. J. J. Chem. Res., Synop. 1991, 216-217. (j) Curran, D. P.; Seong, C. M. Tetrahedron 1992, 48, 2157-2174. (k) Curran, D. P.; Seong, C. M. Tetrahedron 1992, 48, 2175-2190. (l) Maslak, V.; Cekovic, Z.; Saicic, R. N. Synlett 1998, 1435-1437. (m) McCarroll, A. J.; Walton, J. C. J. Chem. Soc., Perkin Trans. 1 2001, 3215-3229. (n) Kitagawa, O.; Fujiwara, H.; Taguchi, T. Tetrahedron Lett. 2001, 42, 2165-2167. (o) Kitagawa, O.; Yamada, Y.; Fujiwara, H.;. Taguchi, T. J. Org. Chem. 2002, 67, 922-927. (p) Kitagawa, O.; Yamada, Y.; Sugawara, A.; Taguchi, T. Org. Lett. 2002, 4, 1011-1013.
14. The reaction with electron-deficient alkenes: (a) Clieve, D. L. J.; Angoh, A. G. J. Chem. Soc., Chem. Commun. 1985, 980-982. (b) Cekovik, Z.; Saicic, R. Tetrahedron Lett. 1986, 27, 5893-5896. (c) Curran, D. P.; Chen, M. J. Am. Chem. Soc. 1987, 109, 6558-6560. (d) Barton, D. H. R.; Zard, S. Z.; daSilva, E. J. Chem. Soc., Chem. Commun. 1988, 285-287. (e) Feldman, K. S.; Romanelli, A. L.; Ruckle, R. E., Jr.; Miller, R. F. J. Am. Chem. Soc. 1988, 110, 3300-3302. (f) Curran, D. P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I. Eds.; Pergamon Press: New York, 1991; Vol. 4, pp 779-831 and references therein. The reaction with simple alkenes: (g) Miura, K.; Fugami, K.; Ohshima, K.; Utimoto, K. Tetrahedron Lett. 1988, 29, 5135-5138. (h) Curran, D. P.; Chen, M.; Spletzer, E. J. Am. Chem. Soc. 1989, 111, 8872-8878. (i) Chuang, C. P.; Hou, S. S.; Ngoi, T. H. J. J. Chem. Res., Synop. 1991, 216-217. (j) Curran, D. P.; Seong, C. M. Tetrahedron 1992, 48, 2157-2174. (k) Curran, D. P.; Seong, C. M. Tetrahedron 1992, 48, 2175-2190. (l) Maslak, V.; Cekovic, Z.; Saicic, R. N. Synlett 1998, 1435-1437. (m) McCarroll, A. J.; Walton, J. C. J. Chem. Soc., Perkin Trans. 1 2001, 3215-3229. (n) Kitagawa, O.; Fujiwara, H.; Taguchi, T. Tetrahedron Lett. 2001, 42, 2165-2167. (o) Kitagawa, O.; Yamada, Y.; Fujiwara, H.;. Taguchi, T. J. Org. Chem. 2002, 67, 922-927. (p) Kitagawa, O.; Yamada, Y.; Sugawara, A.; Taguchi, T. Org. Lett. 2002, 4, 1011-1013.
15. The reaction with electron-deficient alkenes: (a) Clieve, D. L. J.; Angoh, A. G. J. Chem. Soc., Chem. Commun. 1985, 980-982. (b) Cekovik, Z.; Saicic, R. Tetrahedron Lett. 1986, 27, 5893-5896. (c) Curran, D. P.; Chen, M. J. Am. Chem. Soc. 1987, 109, 6558-6560. (d) Barton, D. H. R.; Zard, S. Z.; daSilva, E. J. Chem. Soc., Chem. Commun. 1988, 285-287. (e) Feldman, K. S.; Romanelli, A. L.; Ruckle, R. E., Jr.; Miller, R. F. J. Am. Chem. Soc. 1988, 110, 3300-3302. (f) Curran, D. P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I. Eds.; Pergamon Press: New York, 1991; Vol. 4, pp 779-831 and references therein. The reaction with simple alkenes: (g) Miura, K.; Fugami, K.; Ohshima, K.; Utimoto, K. Tetrahedron Lett. 1988, 29, 5135-5138. (h) Curran, D. P.; Chen, M.; Spletzer, E. J. Am. Chem. Soc. 1989, 111, 8872-8878. (i) Chuang, C. P.; Hou, S. S.; Ngoi, T. H. J. J. Chem. Res., Synop. 1991, 216-217. (j) Curran, D. P.; Seong, C. M. Tetrahedron 1992, 48, 2157-2174. (k) Curran, D. P.; Seong, C. M. Tetrahedron 1992, 48, 2175-2190. (l) Maslak, V.; Cekovic, Z.; Saicic, R. N. Synlett 1998, 1435-1437. (m) McCarroll, A. J.; Walton, J. C. J. Chem. Soc., Perkin Trans. 1 2001, 3215-3229. (n) Kitagawa, O.; Fujiwara, H.; Taguchi, T. Tetrahedron Lett. 2001, 42, 2165-2167. (o) Kitagawa, O.; Yamada, Y.; Fujiwara, H.;. Taguchi, T. J. Org. Chem. 2002, 67, 922-927. (p) Kitagawa, O.; Yamada, Y.; Sugawara, A.; Taguchi, T. Org. Lett. 2002, 4, 1011-1013.
16. The reaction with electron-deficient alkenes: (a) Clieve, D. L. J.; Angoh, A. G. J. Chem. Soc., Chem. Commun. 1985, 980-982. (b) Cekovik, Z.; Saicic, R. Tetrahedron Lett. 1986, 27, 5893-5896. (c) Curran, D. P.; Chen, M. J. Am. Chem. Soc. 1987, 109, 6558-6560. (d) Barton, D. H. R.; Zard, S. Z.; daSilva, E. J. Chem. Soc., Chem. Commun. 1988, 285-287. (e) Feldman, K. S.; Romanelli, A. L.; Ruckle, R. E., Jr.; Miller, R. F. J. Am. Chem. Soc. 1988, 110, 3300-3302. (f) Curran, D. P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I. Eds.; Pergamon Press: New York, 1991; Vol. 4, pp 779-831 and references therein. The reaction with simple alkenes: (g) Miura, K.; Fugami, K.; Ohshima, K.; Utimoto, K. Tetrahedron Lett. 1988, 29, 5135-5138. (h) Curran, D. P.; Chen, M.; Spletzer, E. J. Am. Chem. Soc. 1989, 111, 8872-8878. (i) Chuang, C. P.; Hou, S. S.; Ngoi, T. H. J. J. Chem. Res., Synop. 1991, 216-217. (j) Curran, D. P.; Seong, C. M. Tetrahedron 1992, 48, 2157-2174. (k) Curran, D. P.; Seong, C. M. Tetrahedron 1992, 48, 2175-2190. (l) Maslak, V.; Cekovic, Z.; Saicic, R. N. Synlett 1998, 1435-1437. (m) McCarroll, A. J.; Walton, J. C. J. Chem. Soc., Perkin Trans. 1 2001, 3215-3229. (n) Kitagawa, O.; Fujiwara, H.; Taguchi, T. Tetrahedron Lett. 2001, 42, 2165-2167. (o) Kitagawa, O.; Yamada, Y.; Fujiwara, H.;. Taguchi, T. J. Org. Chem. 2002, 67, 922-927. (p) Kitagawa, O.; Yamada, Y.; Sugawara, A.; Taguchi, T. Org. Lett. 2002, 4, 1011-1013.
17. Newcomb, M.; Kumar, M. U. Tetrahedron Lett. 1990, 31, 1675-1678.
18. (a) Stella, L. Angew. Chem., Int. Ed. Engl. 1983, 22, 337-350.
19. (b) Esker, J. L.; Newcomb, M. In Advances in Heterocyclic Chemistry; Katritzky, A. R., Ed.; Academic Press: San Diego, 1993; Vol. 58, pp 1-45.
20. (c) Fallis, A. G.; Brinza, I. M. Tetrahedron 1997, 53, 17543-17593.
21. For a review, see: Mackiewicz, P.; Furstoss, R. Tetrahedron 1978, 34, 3241-3260.
22. (a) Newcomb, M.; Burchill, M. T.; Deeb, T. M. J. Am. Chem. Soc. 1988, 110, 6528-6535.
23. (b) Musa, O. M.; Horner, J. H.; Shahin, H.; Newcomb, M. J. Am. Chem. Soc. 1996, 118, 3862-3868.
24. It has been well-known that electrophilic aminium cation radicals and metal-complexed aminyl radicals formed by the addition of Brønsted acid and Lewis acid are more reactive to alkenes than simple aminyl radicals. (a) Neals, R. S.; Marcus, N. L. J. Org. Chem. 1967, 32, 3273-3284. (b) Surzur, J. M.; Stella, L.; Tordo, P. Bull. Soc. Chim. Fr. 1970, 115-120. (c) Neale, R. S. Synthesis 1971, 1-15. (d) Dickinson, J. M.; Murphy, J. A. J. Chem Soc., Chem. Commun. 1990, 434-436. (e) Ha, C.; Musa, O.; Martinez, M. F.; Newcomb, M. J. Org. Chem. 1997, 32, 2704-2710. (f) Hemmerling, M.; Sjöholm, A.; Somfai, P. Tetrahedron: Asymmetry 1999, 10, 4091-4094 and references therein.
25. It has been well-known that electrophilic aminium cation radicals and metal-complexed aminyl radicals formed by the addition of Brønsted acid and Lewis acid are more reactive to alkenes than simple aminyl radicals. (a) Neals, R. S.; Marcus, N. L. J. Org. Chem. 1967, 32, 3273-3284. (b) Surzur, J. M.; Stella, L.; Tordo, P. Bull. Soc. Chim. Fr. 1970, 115-120. (c) Neale, R. S. Synthesis 1971, 1-15. (d) Dickinson, J. M.; Murphy, J. A. J. Chem Soc., Chem. Commun. 1990, 434-436. (e) Ha, C.; Musa, O.; Martinez, M. F.; Newcomb, M. J. Org. Chem. 1997, 32, 2704-2710. (f) Hemmerling, M.; Sjöholm, A.; Somfai, P. Tetrahedron: Asymmetry 1999, 10, 4091-4094 and references therein.
26. It has been well-known that electrophilic aminium cation radicals and metal-complexed aminyl radicals formed by the addition of Brønsted acid and Lewis acid are more reactive to alkenes than simple aminyl radicals. (a) Neals, R. S.; Marcus, N. L. J. Org. Chem. 1967, 32, 3273-3284. (b) Surzur, J. M.; Stella, L.; Tordo, P. Bull. Soc. Chim. Fr. 1970, 115-120. (c) Neale, R. S. Synthesis 1971, 1-15. (d) Dickinson, J. M.; Murphy, J. A. J. Chem Soc., Chem. Commun. 1990, 434-436. (e) Ha, C.; Musa, O.; Martinez, M. F.; Newcomb, M. J. Org. Chem. 1997, 32, 2704-2710. (f) Hemmerling, M.; Sjöholm, A.; Somfai, P. Tetrahedron: Asymmetry 1999, 10, 4091-4094 and references therein.
27. It has been well-known that electrophilic aminium cation radicals and metal-complexed aminyl radicals formed by the addition of Brønsted acid and Lewis acid are more reactive to alkenes than simple aminyl radicals. (a) Neals, R. S.; Marcus, N. L. J. Org. Chem. 1967, 32, 3273-3284. (b) Surzur, J. M.; Stella, L.; Tordo, P. Bull. Soc. Chim. Fr. 1970, 115-120. (c) Neale, R. S. Synthesis 1971, 1-15. (d) Dickinson, J. M.; Murphy, J. A. J. Chem Soc., Chem. Commun. 1990, 434-436. (e) Ha, C.; Musa, O.; Martinez, M. F.; Newcomb, M. J. Org. Chem. 1997, 32, 2704-2710. (f) Hemmerling, M.; Sjöholm, A.; Somfai, P. Tetrahedron: Asymmetry 1999, 10, 4091-4094 and references therein.
28. It has been well-known that electrophilic aminium cation radicals and metal-complexed aminyl radicals formed by the addition of Brønsted acid and Lewis acid are more reactive to alkenes than simple aminyl radicals. (a) Neals, R. S.; Marcus, N. L. J. Org. Chem. 1967, 32, 3273-3284. (b) Surzur, J. M.; Stella, L.; Tordo, P. Bull. Soc. Chim. Fr. 1970, 115-120. (c) Neale, R. S. Synthesis 1971, 1-15. (d) Dickinson, J. M.; Murphy, J. A. J. Chem Soc., Chem. Commun. 1990, 434-436. (e) Ha, C.; Musa, O.; Martinez, M. F.; Newcomb, M. J. Org. Chem. 1997, 32, 2704-2710. (f) Hemmerling, M.; Sjöholm, A.; Somfai, P. Tetrahedron: Asymmetry 1999, 10, 4091-4094 and references therein.
29. It has been well-known that electrophilic aminium cation radicals and metal-complexed aminyl radicals formed by the addition of Brønsted acid and Lewis acid are more reactive to alkenes than simple aminyl radicals. (a) Neals, R. S.; Marcus, N. L. J. Org. Chem. 1967, 32, 3273-3284. (b) Surzur, J. M.; Stella, L.; Tordo, P. Bull. Soc. Chim. Fr. 1970, 115-120. (c) Neale, R. S. Synthesis 1971, 1-15. (d) Dickinson, J. M.; Murphy, J. A. J. Chem Soc., Chem. Commun. 1990, 434-436. (e) Ha, C.; Musa, O.; Martinez, M. F.; Newcomb, M. J. Org. Chem. 1997, 32, 2704-2710. (f) Hemmerling, M.; Sjöholm, A.; Somfai, P. Tetrahedron: Asymmetry 1999, 10, 4091-4094 and references therein.
30. Our preliminary communication: Kitagawa, O.; Yamada, Y.; Fujiwara, H.; Taguchi, T. Angew. Chem., Int. Ed. 2001, 40, 3865-3867.
31. Tsuritani, T.; Shinokubo, H.; Ohshima, K. Org. Lett. 2001, 3, 2709-2711.
32. Reports in relation to regioselective cleavage of aziridinylcarbinyl radicals and their application to intramolecular radical cyclization: (a) Dickinson, J. M.; Murphy, J. A. Tetrahedron 1992, 48, 1317-1326. (b) De Kimpe, N.; Jolie, R.; De Smaele, D. J. Chem Soc., Chem. Commun. 1994, 1221-1222. (c) De Smaele, D.; Bogaert, P.; De Kimpe, N. Tetrahedron Lett. 1998, 39, 9797-9800. (d) For a review, see: Li, J. J. Tetrahedron 2001, 57, 1-24.
33. Reports in relation to regioselective cleavage of aziridinylcarbinyl radicals and their application to intramolecular radical cyclization: (a) Dickinson, J. M.; Murphy, J. A. Tetrahedron 1992, 48, 1317-1326. (b) De Kimpe, N.; Jolie, R.; De Smaele, D. J. Chem Soc., Chem. Commun. 1994, 1221-1222. (c) De Smaele, D.; Bogaert, P.; De Kimpe, N. Tetrahedron Lett. 1998, 39, 9797-9800. (d) For a review, see: Li, J. J. Tetrahedron 2001, 57, 1-24.
34. Reports in relation to regioselective cleavage of aziridinylcarbinyl radicals and their application to intramolecular radical cyclization: (a) Dickinson, J. M.; Murphy, J. A. Tetrahedron 1992, 48, 1317-1326. (b) De Kimpe, N.; Jolie, R.; De Smaele, D. J. Chem Soc., Chem. Commun. 1994, 1221-1222. (c) De Smaele, D.; Bogaert, P.; De Kimpe, N. Tetrahedron Lett. 1998, 39, 9797-9800. (d) For a review, see: Li, J. J. Tetrahedron 2001, 57, 1-24.
35. Reports in relation to regioselective cleavage of aziridinylcarbinyl radicals and their application to intramolecular radical cyclization: (a) Dickinson, J. M.; Murphy, J. A. Tetrahedron 1992, 48, 1317-1326. (b) De Kimpe, N.; Jolie, R.; De Smaele, D. J. Chem Soc., Chem. Commun. 1994, 1221-1222. (c) De Smaele, D.; Bogaert, P.; De Kimpe, N. Tetrahedron Lett. 1998, 39, 9797-9800. (d) For a review, see: Li, J. J. Tetrahedron 2001, 57, 1-24.
36. Since the formation of an aziridinyl methyl radical is a thermodynamically favorable process, an iodine-transfer process leading to the resulting pyrrolidinyl methyl radical intermediate from iodoaziridine 1 should proceed efficiently.
37. Horner, J. H.; Musa, O.; Bouvier, M. A.; Newcomb, M. J. Am. Chem. Soc. 1998, 120, 7738-7748.
38. Kitagawa, O.; Suzuki, T.; Taguchi, T. J. Org. Chem. 1998, 63, 4842-4845.
39. Oshima, K.; Uchimoto, K. J. Synth. Org. Chem. Jpn. 1989, 47, 40-50.
40. 3B-mediated method.
41. 13C chemical shift of the iodomethyl group is also useful for the determination of the stereochemistry. For example, the chemical shift of the iodomethyl group in cis-isomers of 2a, 3a, 3b, 4a, and 8a appears upfield from that of trans-isomers.
42. In the preliminary communication (ref 7), the diastereomer ratio (α-2d/β-2d = 1/1.5, α-2e/β-2e = 1.4) which corresponds to compound 3d and 3e in this paper, was found to be a typographical errors due to our carelessness. As shown in entries 4 and 5 of Table 2, we must now correct the ratio as α-2d/β-2d = 1.5 and α-2e/β-2e = 1/1.4 in ref 7.
43. The model to rationalize such endo selectivity in the bicyclo[3.3.0]octane system has been reported by Curran and co-workers: Curran, D. P.; Rakiewicz, D. M. Tetrahedron 1985, 41, 3943-3953.
44. 2 atmosphere.
45. Recent reports in relation to hydroindole alkaloids: (a) Banker, R.; Carmeli, S. Tetrahedron 1999, 55, 10835-10844. (b) Valls, N.; Vallribera, M.; López-Canet, M.; Bonjoch, J. J. Org. Chem. 2002, 67, 4945-4950. (c) Ishida, K.; Okita, H.; Matsuda, H.; Okino, T.; Murakami, M. Tetrahedron 1999, 55, 10971-10988. (d) Valls, N.; LópezCanet, M.; Vallribera, M.; Bonjoch, J. Chem. Eur. J. 2001, 7, 3446-3460. (e) Wipf, P.; Methot, J.-L. Org. Lett. 2000, 2, 4231-4216. (f) Padwa, A.; Brodney, M. A.; Lynch, S. M. J. Org. Chem. 2001, 66, 1716-1724. (g) Tamura, O.; Matsukida, H.; Toyao, A.; Takeda, Y.; Ishibashi, H. J. Org. Chem. 2002, 67, 5537-5545.
46. Recent reports in relation to hydroindole alkaloids: (a) Banker, R.; Carmeli, S. Tetrahedron 1999, 55, 10835-10844. (b) Valls, N.; Vallribera, M.; López-Canet, M.; Bonjoch, J. J. Org. Chem. 2002, 67, 4945-4950. (c) Ishida, K.; Okita, H.; Matsuda, H.; Okino, T.; Murakami, M. Tetrahedron 1999, 55, 10971-10988. (d) Valls, N.; LópezCanet, M.; Vallribera, M.; Bonjoch, J. Chem. Eur. J. 2001, 7, 3446-3460. (e) Wipf, P.; Methot, J.-L. Org. Lett. 2000, 2, 4231-4216. (f) Padwa, A.; Brodney, M. A.; Lynch, S. M. J. Org. Chem. 2001, 66, 1716-1724. (g) Tamura, O.; Matsukida, H.; Toyao, A.; Takeda, Y.; Ishibashi, H. J. Org. Chem. 2002, 67, 5537-5545.
47. Recent reports in relation to hydroindole alkaloids: (a) Banker, R.; Carmeli, S. Tetrahedron 1999, 55, 10835-10844. (b) Valls, N.; Vallribera, M.; López-Canet, M.; Bonjoch, J. J. Org. Chem. 2002, 67, 4945-4950. (c) Ishida, K.; Okita, H.; Matsuda, H.; Okino, T.; Murakami, M. Tetrahedron 1999, 55, 10971-10988. (d) Valls, N.; LópezCanet, M.; Vallribera, M.; Bonjoch, J. Chem. Eur. J. 2001, 7, 3446-3460. (e) Wipf, P.; Methot, J.-L. Org. Lett. 2000, 2, 4231-4216. (f) Padwa, A.; Brodney, M. A.; Lynch, S. M. J. Org. Chem. 2001, 66, 1716-1724. (g) Tamura, O.; Matsukida, H.; Toyao, A.; Takeda, Y.; Ishibashi, H. J. Org. Chem. 2002, 67, 5537-5545.
48. Recent reports in relation to hydroindole alkaloids: (a) Banker, R.; Carmeli, S. Tetrahedron 1999, 55, 10835-10844. (b) Valls, N.; Vallribera, M.; López-Canet, M.; Bonjoch, J. J. Org. Chem. 2002, 67, 4945-4950. (c) Ishida, K.; Okita, H.; Matsuda, H.; Okino, T.; Murakami, M. Tetrahedron 1999, 55, 10971-10988. (d) Valls, N.; LópezCanet, M.; Vallribera, M.; Bonjoch, J. Chem. Eur. J. 2001, 7, 3446-3460. (e) Wipf, P.; Methot, J.-L. Org. Lett. 2000, 2, 4231-4216. (f) Padwa, A.; Brodney, M. A.; Lynch, S. M. J. Org. Chem. 2001, 66, 1716-1724. (g) Tamura, O.; Matsukida, H.; Toyao, A.; Takeda, Y.; Ishibashi, H. J. Org. Chem. 2002, 67, 5537-5545.
49. Recent reports in relation to hydroindole alkaloids: (a) Banker, R.; Carmeli, S. Tetrahedron 1999, 55, 10835-10844. (b) Valls, N.; Vallribera, M.; López-Canet, M.; Bonjoch, J. J. Org. Chem. 2002, 67, 4945-4950. (c) Ishida, K.; Okita, H.; Matsuda, H.; Okino, T.; Murakami, M. Tetrahedron 1999, 55, 10971-10988. (d) Valls, N.; LópezCanet, M.; Vallribera, M.; Bonjoch, J. Chem. Eur. J. 2001, 7, 3446-3460. (e) Wipf, P.; Methot, J.-L. Org. Lett. 2000, 2, 4231-4216. (f) Padwa, A.; Brodney, M. A.; Lynch, S. M. J. Org. Chem. 2001, 66, 1716-1724. (g) Tamura, O.; Matsukida, H.; Toyao, A.; Takeda, Y.; Ishibashi, H. J. Org. Chem. 2002, 67, 5537-5545.
50. Recent reports in relation to hydroindole alkaloids: (a) Banker, R.; Carmeli, S. Tetrahedron 1999, 55, 10835-10844. (b) Valls, N.; Vallribera, M.; López-Canet, M.; Bonjoch, J. J. Org. Chem. 2002, 67, 4945-4950. (c) Ishida, K.; Okita, H.; Matsuda, H.; Okino, T.; Murakami, M. Tetrahedron 1999, 55, 10971-10988. (d) Valls, N.; LópezCanet, M.; Vallribera, M.; Bonjoch, J. Chem. Eur. J. 2001, 7, 3446-3460. (e) Wipf, P.; Methot, J.-L. Org. Lett. 2000, 2, 4231-4216. (f) Padwa, A.; Brodney, M. A.; Lynch, S. M. J. Org. Chem. 2001, 66, 1716-1724. (g) Tamura, O.; Matsukida, H.; Toyao, A.; Takeda, Y.; Ishibashi, H. J. Org. Chem. 2002, 67, 5537-5545.
51. Recent reports in relation to hydroindole alkaloids: (a) Banker, R.; Carmeli, S. Tetrahedron 1999, 55, 10835-10844. (b) Valls, N.; Vallribera, M.; López-Canet, M.; Bonjoch, J. J. Org. Chem. 2002, 67, 4945-4950. (c) Ishida, K.; Okita, H.; Matsuda, H.; Okino, T.; Murakami, M. Tetrahedron 1999, 55, 10971-10988. (d) Valls, N.; LópezCanet, M.; Vallribera, M.; Bonjoch, J. Chem. Eur. J. 2001, 7, 3446-3460. (e) Wipf, P.; Methot, J.-L. Org. Lett. 2000, 2, 4231-4216. (f) Padwa, A.; Brodney, M. A.; Lynch, S. M. J. Org. Chem. 2001, 66, 1716-1724. (g) Tamura, O.; Matsukida, H.; Toyao, A.; Takeda, Y.; Ishibashi, H. J. Org. Chem. 2002, 67, 5537-5545.
52. (a) Trost, B. M.; Vranken, D. L. V.; Bingel, C. J. Am. Chem. Soc. 1992, 114, 9327-9343.
53. (b) Trost, B. M.; Patterson, D. E. J. Org. Chem. 1998, 63, 1339-1341.
54. (c) Stragies, R.; Blechert, S. J. Am. Chem. Soc. 2000, 122, 9584-9591.
55. (a) Müller, P.; Nury, P. Helv. Chim. Acta 2001, 84, 662-678.
56. (b) Kohmura, Y.; Katsuki, T. Tetrahedron Lett. 2001, 42, 3339-3342.