Efficient Medium-Ring Cyclization under Non-High-Dilution Conditions Using Sml2

Organic Letters

Volumn 6, Issue 4, 2004, Pages 545-547

  Tamiya, Hiroaki ^a   Goto, Kazuhiro ^a   Matsuda, Fuyuhiko ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

SAMARIUM DIIODIDE;

ARTICLE; CYCLIZATION; DILUTION; QUANTITATIVE ANALYSIS; SYNTHESIS;

EID: 1342311484     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol036329h     Document Type: Article

References (51)

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8. 2. See: (a) Kan, T.; Matsuda, F.; Yanagiya, M.; Shirahama, H. Synlett 1991, 391. (b) Kito, M.; Sakai, T.; Yamada, K.; Matsuda, F.; Shirahama, H. Synlett 1993, 158. (c) Kan, T.; Nara, S.; Ito, S.; Matsuda, F.; Shirahama, H. J. Org. Chem. 1994, 59, 5111. (d) Kan, T.; Hosokawa, S.; Nara, S.; Oikawa, M.; Ito, S.; Matsuda, F.; Shirahama, H. J. Org. Chem. 1994, 59, 5532. (e) Kawatsura, M.; Matsuda, F.; Shirahama, H. J. Org. Chem. 1994, 59, 6900. (f) Kawatsura, M.; Hosaka, K.; Matsuda, F.; Shirahama, H. Synlett 1995, 729. (g) Matsuda, F. J. Synth. Org. Chem. Jpn. 1995, 53, 987. (h) Kawatsura, M. ; Dekura, F.; Shirahama, H.; Matsuda, F. Synlett 1996, 373. (i) Kito, M.; Sakai, T.; Haruta, N.; Shirahama, H.; Matsuda, F. Synlett 1996, 1057. (j) Kawatsura, M.; Kishi, E.; Kito, M.; Sakai, T.; Shirahama, H.; Matsuda, F. Synlett 1997, 479. (k) Matsuda, F.; Kawatsura, M.; Dekura, F.; Shirahama, H. J. Chem. Soc., Perkin Trans. 1 1999, 2371. (l) Matsuda, F.; Kawatsura, M.; Hosaka, K.; Shirahama, H. Chem. Eur. J. 1999, 5, 3252. (m) Kan, T.; Nara, S.; Ozawa, T.; Shirahama, H.; Matsuda, F. Angew. Chem., Int. Ed. 2000, 39, 355.
9. 2. See: (a) Kan, T.; Matsuda, F.; Yanagiya, M.; Shirahama, H. Synlett 1991, 391. (b) Kito, M.; Sakai, T.; Yamada, K.; Matsuda, F.; Shirahama, H. Synlett 1993, 158. (c) Kan, T.; Nara, S.; Ito, S.; Matsuda, F.; Shirahama, H. J. Org. Chem. 1994, 59, 5111. (d) Kan, T.; Hosokawa, S.; Nara, S.; Oikawa, M.; Ito, S.; Matsuda, F.; Shirahama, H. J. Org. Chem. 1994, 59, 5532. (e) Kawatsura, M.; Matsuda, F.; Shirahama, H. J. Org. Chem. 1994, 59, 6900. (f) Kawatsura, M.; Hosaka, K.; Matsuda, F.; Shirahama, H. Synlett 1995, 729. (g) Matsuda, F. J. Synth. Org. Chem. Jpn. 1995, 53, 987. (h) Kawatsura, M. ; Dekura, F.; Shirahama, H.; Matsuda, F. Synlett 1996, 373. (i) Kito, M.; Sakai, T.; Haruta, N.; Shirahama, H.; Matsuda, F. Synlett 1996, 1057. (j) Kawatsura, M.; Kishi, E.; Kito, M.; Sakai, T.; Shirahama, H.; Matsuda, F. Synlett 1997, 479. (k) Matsuda, F.; Kawatsura, M.; Dekura, F.; Shirahama, H. J. Chem. Soc., Perkin Trans. 1 1999, 2371. (l) Matsuda, F.; Kawatsura, M.; Hosaka, K.; Shirahama, H. Chem. Eur. J. 1999, 5, 3252. (m) Kan, T.; Nara, S.; Ozawa, T.; Shirahama, H.; Matsuda, F. Angew. Chem., Int. Ed. 2000, 39, 355.
10. 2. See: (a) Kan, T.; Matsuda, F.; Yanagiya, M.; Shirahama, H. Synlett 1991, 391. (b) Kito, M.; Sakai, T.; Yamada, K.; Matsuda, F.; Shirahama, H. Synlett 1993, 158. (c) Kan, T.; Nara, S.; Ito, S.; Matsuda, F.; Shirahama, H. J. Org. Chem. 1994, 59, 5111. (d) Kan, T.; Hosokawa, S.; Nara, S.; Oikawa, M.; Ito, S.; Matsuda, F.; Shirahama, H. J. Org. Chem. 1994, 59, 5532. (e) Kawatsura, M.; Matsuda, F.; Shirahama, H. J. Org. Chem. 1994, 59, 6900. (f) Kawatsura, M.; Hosaka, K.; Matsuda, F.; Shirahama, H. Synlett 1995, 729. (g) Matsuda, F. J. Synth. Org. Chem. Jpn. 1995, 53, 987. (h) Kawatsura, M. ; Dekura, F.; Shirahama, H.; Matsuda, F. Synlett 1996, 373. (i) Kito, M.; Sakai, T.; Haruta, N.; Shirahama, H.; Matsuda, F. Synlett 1996, 1057. (j) Kawatsura, M.; Kishi, E.; Kito, M.; Sakai, T.; Shirahama, H.; Matsuda, F. Synlett 1997, 479. (k) Matsuda, F.; Kawatsura, M.; Dekura, F.; Shirahama, H. J. Chem. Soc., Perkin Trans. 1 1999, 2371. (l) Matsuda, F.; Kawatsura, M.; Hosaka, K.; Shirahama, H. Chem. Eur. J. 1999, 5, 3252. (m) Kan, T.; Nara, S.; Ozawa, T.; Shirahama, H.; Matsuda, F. Angew. Chem., Int. Ed. 2000, 39, 355.
11. 2. See: (a) Kan, T.; Matsuda, F.; Yanagiya, M.; Shirahama, H. Synlett 1991, 391. (b) Kito, M.; Sakai, T.; Yamada, K.; Matsuda, F.; Shirahama, H. Synlett 1993, 158. (c) Kan, T.; Nara, S.; Ito, S.; Matsuda, F.; Shirahama, H. J. Org. Chem. 1994, 59, 5111. (d) Kan, T.; Hosokawa, S.; Nara, S.; Oikawa, M.; Ito, S.; Matsuda, F.; Shirahama, H. J. Org. Chem. 1994, 59, 5532. (e) Kawatsura, M.; Matsuda, F.; Shirahama, H. J. Org. Chem. 1994, 59, 6900. (f) Kawatsura, M.; Hosaka, K.; Matsuda, F.; Shirahama, H. Synlett 1995, 729. (g) Matsuda, F. J. Synth. Org. Chem. Jpn. 1995, 53, 987. (h) Kawatsura, M. ; Dekura, F.; Shirahama, H.; Matsuda, F. Synlett 1996, 373. (i) Kito, M.; Sakai, T.; Haruta, N.; Shirahama, H.; Matsuda, F. Synlett 1996, 1057. (j) Kawatsura, M.; Kishi, E.; Kito, M.; Sakai, T.; Shirahama, H.; Matsuda, F. Synlett 1997, 479. (k) Matsuda, F.; Kawatsura, M.; Dekura, F.; Shirahama, H. J. Chem. Soc., Perkin Trans. 1 1999, 2371. (l) Matsuda, F.; Kawatsura, M.; Hosaka, K.; Shirahama, H. Chem. Eur. J. 1999, 5, 3252. (m) Kan, T.; Nara, S.; Ozawa, T.; Shirahama, H.; Matsuda, F. Angew. Chem., Int. Ed. 2000, 39, 355.
12. 2. See: (a) Kan, T.; Matsuda, F.; Yanagiya, M.; Shirahama, H. Synlett 1991, 391. (b) Kito, M.; Sakai, T.; Yamada, K.; Matsuda, F.; Shirahama, H. Synlett 1993, 158. (c) Kan, T.; Nara, S.; Ito, S.; Matsuda, F.; Shirahama, H. J. Org. Chem. 1994, 59, 5111. (d) Kan, T.; Hosokawa, S.; Nara, S.; Oikawa, M.; Ito, S.; Matsuda, F.; Shirahama, H. J. Org. Chem. 1994, 59, 5532. (e) Kawatsura, M.; Matsuda, F.; Shirahama, H. J. Org. Chem. 1994, 59, 6900. (f) Kawatsura, M.; Hosaka, K.; Matsuda, F.; Shirahama, H. Synlett 1995, 729. (g) Matsuda, F. J. Synth. Org. Chem. Jpn. 1995, 53, 987. (h) Kawatsura, M. ; Dekura, F.; Shirahama, H.; Matsuda, F. Synlett 1996, 373. (i) Kito, M.; Sakai, T.; Haruta, N.; Shirahama, H.; Matsuda, F. Synlett 1996, 1057. (j) Kawatsura, M.; Kishi, E.; Kito, M.; Sakai, T.; Shirahama, H.; Matsuda, F. Synlett 1997, 479. (k) Matsuda, F.; Kawatsura, M.; Dekura, F.; Shirahama, H. J. Chem. Soc., Perkin Trans. 1 1999, 2371. (l) Matsuda, F.; Kawatsura, M.; Hosaka, K.; Shirahama, H. Chem. Eur. J. 1999, 5, 3252. (m) Kan, T.; Nara, S.; Ozawa, T.; Shirahama, H.; Matsuda, F. Angew. Chem., Int. Ed. 2000, 39, 355.
13. 2. See: (a) Kan, T.; Matsuda, F.; Yanagiya, M.; Shirahama, H. Synlett 1991, 391. (b) Kito, M.; Sakai, T.; Yamada, K.; Matsuda, F.; Shirahama, H. Synlett 1993, 158. (c) Kan, T.; Nara, S.; Ito, S.; Matsuda, F.; Shirahama, H. J. Org. Chem. 1994, 59, 5111. (d) Kan, T.; Hosokawa, S.; Nara, S.; Oikawa, M.; Ito, S.; Matsuda, F.; Shirahama, H. J. Org. Chem. 1994, 59, 5532. (e) Kawatsura, M.; Matsuda, F.; Shirahama, H. J. Org. Chem. 1994, 59, 6900. (f) Kawatsura, M.; Hosaka, K.; Matsuda, F.; Shirahama, H. Synlett 1995, 729. (g) Matsuda, F. J. Synth. Org. Chem. Jpn. 1995, 53, 987. (h) Kawatsura, M. ; Dekura, F.; Shirahama, H.; Matsuda, F. Synlett 1996, 373. (i) Kito, M.; Sakai, T.; Haruta, N.; Shirahama, H.; Matsuda, F. Synlett 1996, 1057. (j) Kawatsura, M.; Kishi, E.; Kito, M.; Sakai, T.; Shirahama, H.; Matsuda, F. Synlett 1997, 479. (k) Matsuda, F.; Kawatsura, M.; Dekura, F.; Shirahama, H. J. Chem. Soc., Perkin Trans. 1 1999, 2371. (l) Matsuda, F.; Kawatsura, M.; Hosaka, K.; Shirahama, H. Chem. Eur. J. 1999, 5, 3252. (m) Kan, T.; Nara, S.; Ozawa, T.; Shirahama, H.; Matsuda, F. Angew. Chem., Int. Ed. 2000, 39, 355.
14. 2. See: (a) Kan, T.; Matsuda, F.; Yanagiya, M.; Shirahama, H. Synlett 1991, 391. (b) Kito, M.; Sakai, T.; Yamada, K.; Matsuda, F.; Shirahama, H. Synlett 1993, 158. (c) Kan, T.; Nara, S.; Ito, S.; Matsuda, F.; Shirahama, H. J. Org. Chem. 1994, 59, 5111. (d) Kan, T.; Hosokawa, S.; Nara, S.; Oikawa, M.; Ito, S.; Matsuda, F.; Shirahama, H. J. Org. Chem. 1994, 59, 5532. (e) Kawatsura, M.; Matsuda, F.; Shirahama, H. J. Org. Chem. 1994, 59, 6900. (f) Kawatsura, M.; Hosaka, K.; Matsuda, F.; Shirahama, H. Synlett 1995, 729. (g) Matsuda, F. J. Synth. Org. Chem. Jpn. 1995, 53, 987. (h) Kawatsura, M. ; Dekura, F.; Shirahama, H.; Matsuda, F. Synlett 1996, 373. (i) Kito, M.; Sakai, T.; Haruta, N.; Shirahama, H.; Matsuda, F. Synlett 1996, 1057. (j) Kawatsura, M.; Kishi, E.; Kito, M.; Sakai, T.; Shirahama, H.; Matsuda, F. Synlett 1997, 479. (k) Matsuda, F.; Kawatsura, M.; Dekura, F.; Shirahama, H. J. Chem. Soc., Perkin Trans. 1 1999, 2371. (l) Matsuda, F.; Kawatsura, M.; Hosaka, K.; Shirahama, H. Chem. Eur. J. 1999, 5, 3252. (m) Kan, T.; Nara, S.; Ozawa, T.; Shirahama, H.; Matsuda, F. Angew. Chem., Int. Ed. 2000, 39, 355.
15. 2. See: (a) Kan, T.; Matsuda, F.; Yanagiya, M.; Shirahama, H. Synlett 1991, 391. (b) Kito, M.; Sakai, T.; Yamada, K.; Matsuda, F.; Shirahama, H. Synlett 1993, 158. (c) Kan, T.; Nara, S.; Ito, S.; Matsuda, F.; Shirahama, H. J. Org. Chem. 1994, 59, 5111. (d) Kan, T.; Hosokawa, S.; Nara, S.; Oikawa, M.; Ito, S.; Matsuda, F.; Shirahama, H. J. Org. Chem. 1994, 59, 5532. (e) Kawatsura, M.; Matsuda, F.; Shirahama, H. J. Org. Chem. 1994, 59, 6900. (f) Kawatsura, M.; Hosaka, K.; Matsuda, F.; Shirahama, H. Synlett 1995, 729. (g) Matsuda, F. J. Synth. Org. Chem. Jpn. 1995, 53, 987. (h) Kawatsura, M. ; Dekura, F.; Shirahama, H.; Matsuda, F. Synlett 1996, 373. (i) Kito, M.; Sakai, T.; Haruta, N.; Shirahama, H.; Matsuda, F. Synlett 1996, 1057. (j) Kawatsura, M.; Kishi, E.; Kito, M.; Sakai, T.; Shirahama, H.; Matsuda, F. Synlett 1997, 479. (k) Matsuda, F.; Kawatsura, M.; Dekura, F.; Shirahama, H. J. Chem. Soc., Perkin Trans. 1 1999, 2371. (l) Matsuda, F.; Kawatsura, M.; Hosaka, K.; Shirahama, H. Chem. Eur. J. 1999, 5, 3252. (m) Kan, T.; Nara, S.; Ozawa, T.; Shirahama, H.; Matsuda, F. Angew. Chem., Int. Ed. 2000, 39, 355.
16. 2. See: (a) Kan, T.; Matsuda, F.; Yanagiya, M.; Shirahama, H. Synlett 1991, 391. (b) Kito, M.; Sakai, T.; Yamada, K.; Matsuda, F.; Shirahama, H. Synlett 1993, 158. (c) Kan, T.; Nara, S.; Ito, S.; Matsuda, F.; Shirahama, H. J. Org. Chem. 1994, 59, 5111. (d) Kan, T.; Hosokawa, S.; Nara, S.; Oikawa, M.; Ito, S.; Matsuda, F.; Shirahama, H. J. Org. Chem. 1994, 59, 5532. (e) Kawatsura, M.; Matsuda, F.; Shirahama, H. J. Org. Chem. 1994, 59, 6900. (f) Kawatsura, M.; Hosaka, K.; Matsuda, F.; Shirahama, H. Synlett 1995, 729. (g) Matsuda, F. J. Synth. Org. Chem. Jpn. 1995, 53, 987. (h) Kawatsura, M. ; Dekura, F.; Shirahama, H.; Matsuda, F. Synlett 1996, 373. (i) Kito, M.; Sakai, T.; Haruta, N.; Shirahama, H.; Matsuda, F. Synlett 1996, 1057. (j) Kawatsura, M.; Kishi, E.; Kito, M.; Sakai, T.; Shirahama, H.; Matsuda, F. Synlett 1997, 479. (k) Matsuda, F.; Kawatsura, M.; Dekura, F.; Shirahama, H. J. Chem. Soc., Perkin Trans. 1 1999, 2371. (l) Matsuda, F.; Kawatsura, M.; Hosaka, K.; Shirahama, H. Chem. Eur. J. 1999, 5, 3252. (m) Kan, T.; Nara, S.; Ozawa, T.; Shirahama, H.; Matsuda, F. Angew. Chem., Int. Ed. 2000, 39, 355.
17. 2. See: (a) Kan, T.; Matsuda, F.; Yanagiya, M.; Shirahama, H. Synlett 1991, 391. (b) Kito, M.; Sakai, T.; Yamada, K.; Matsuda, F.; Shirahama, H. Synlett 1993, 158. (c) Kan, T.; Nara, S.; Ito, S.; Matsuda, F.; Shirahama, H. J. Org. Chem. 1994, 59, 5111. (d) Kan, T.; Hosokawa, S.; Nara, S.; Oikawa, M.; Ito, S.; Matsuda, F.; Shirahama, H. J. Org. Chem. 1994, 59, 5532. (e) Kawatsura, M.; Matsuda, F.; Shirahama, H. J. Org. Chem. 1994, 59, 6900. (f) Kawatsura, M.; Hosaka, K.; Matsuda, F.; Shirahama, H. Synlett 1995, 729. (g) Matsuda, F. J. Synth. Org. Chem. Jpn. 1995, 53, 987. (h) Kawatsura, M. ; Dekura, F.; Shirahama, H.; Matsuda, F. Synlett 1996, 373. (i) Kito, M.; Sakai, T.; Haruta, N.; Shirahama, H.; Matsuda, F. Synlett 1996, 1057. (j) Kawatsura, M.; Kishi, E.; Kito, M.; Sakai, T.; Shirahama, H.; Matsuda, F. Synlett 1997, 479. (k) Matsuda, F.; Kawatsura, M.; Dekura, F.; Shirahama, H. J. Chem. Soc., Perkin Trans. 1 1999, 2371. (l) Matsuda, F.; Kawatsura, M.; Hosaka, K.; Shirahama, H. Chem. Eur. J. 1999, 5, 3252. (m) Kan, T.; Nara, S.; Ozawa, T.; Shirahama, H.; Matsuda, F. Angew. Chem., Int. Ed. 2000, 39, 355.
18. 2. See: (a) Kan, T.; Matsuda, F.; Yanagiya, M.; Shirahama, H. Synlett 1991, 391. (b) Kito, M.; Sakai, T.; Yamada, K.; Matsuda, F.; Shirahama, H. Synlett 1993, 158. (c) Kan, T.; Nara, S.; Ito, S.; Matsuda, F.; Shirahama, H. J. Org. Chem. 1994, 59, 5111. (d) Kan, T.; Hosokawa, S.; Nara, S.; Oikawa, M.; Ito, S.; Matsuda, F.; Shirahama, H. J. Org. Chem. 1994, 59, 5532. (e) Kawatsura, M.; Matsuda, F.; Shirahama, H. J. Org. Chem. 1994, 59, 6900. (f) Kawatsura, M.; Hosaka, K.; Matsuda, F.; Shirahama, H. Synlett 1995, 729. (g) Matsuda, F. J. Synth. Org. Chem. Jpn. 1995, 53, 987. (h) Kawatsura, M. ; Dekura, F.; Shirahama, H.; Matsuda, F. Synlett 1996, 373. (i) Kito, M.; Sakai, T.; Haruta, N.; Shirahama, H.; Matsuda, F. Synlett 1996, 1057. (j) Kawatsura, M.; Kishi, E.; Kito, M.; Sakai, T.; Shirahama, H.; Matsuda, F. Synlett 1997, 479. (k) Matsuda, F.; Kawatsura, M.; Dekura, F.; Shirahama, H. J. Chem. Soc., Perkin Trans. 1 1999, 2371. (l) Matsuda, F.; Kawatsura, M.; Hosaka, K.; Shirahama, H. Chem. Eur. J. 1999, 5, 3252. (m) Kan, T.; Nara, S.; Ozawa, T.; Shirahama, H.; Matsuda, F. Angew. Chem., Int. Ed. 2000, 39, 355.
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35. 2-induced reactions benefit from the presence of HMPA. See: (a) Otsubo, K.; Inanaga, J.; Yamaguchi, M. Tetrahedron Lett. 1986, 27, 5763. (b) Inanaga, J.; Ishikawa, M.; Yamaguchi, M. Chem. Lett. 1987, 1485. (c) Otsubo, K.; Kawamura, K.; Inanaga, J.; Yamaguchi, M. Chem. Lett. 1987, 1487.
36. 2 is quite understood. See: (a) Hasegawa, E.; Curran, D. P. Tetrahedron Lett. 1993, 34, 1717. (b) Hou, Z.; Wakatsuki, Y. J. Chem. Soc., Chem. Commun. 1994, 1205. (c) Hou, Z.; Zhang, Y.; Wakatsuki, Y. Bull. Chem. Soc. Jpn. 1997, 70, 149. (d) Shabangi, M.; Flowers, R. A., II. Tetrahedron Lett. 1997, 38, 1137. (e) Shotwell, J. B.; Sealy, J. M.; Flowers, R. A., II. J. Org. Chem. 1999, 64, 5251. (f) Shabangi, M.; Kuhlman, M. L.; Flowers, R. A., II. Org. Lett. 1999, 1, 2133. (g) Miller, R. S.; Sealy, J. M.; Shabangi, M.; Kuhlman, M. L.; Fuchs, J. R.; Flowers, R. A., II. J. Am. Chem. Soc. 2000, 122, 7718. (h) Prasad, E.; Flowers, R. A., II. J. Am. Chem. Soc. 2002, 124, 6895.
37. 2 is quite understood. See: (a) Hasegawa, E.; Curran, D. P. Tetrahedron Lett. 1993, 34, 1717. (b) Hou, Z.; Wakatsuki, Y. J. Chem. Soc., Chem. Commun. 1994, 1205. (c) Hou, Z.; Zhang, Y.; Wakatsuki, Y. Bull. Chem. Soc. Jpn. 1997, 70, 149. (d) Shabangi, M.; Flowers, R. A., II. Tetrahedron Lett. 1997, 38, 1137. (e) Shotwell, J. B.; Sealy, J. M.; Flowers, R. A., II. J. Org. Chem. 1999, 64, 5251. (f) Shabangi, M.; Kuhlman, M. L.; Flowers, R. A., II. Org. Lett. 1999, 1, 2133. (g) Miller, R. S.; Sealy, J. M.; Shabangi, M.; Kuhlman, M. L.; Fuchs, J. R.; Flowers, R. A., II. J. Am. Chem. Soc. 2000, 122, 7718. (h) Prasad, E.; Flowers, R. A., II. J. Am. Chem. Soc. 2002, 124, 6895.
38. 2 is quite understood. See: (a) Hasegawa, E.; Curran, D. P. Tetrahedron Lett. 1993, 34, 1717. (b) Hou, Z.; Wakatsuki, Y. J. Chem. Soc., Chem. Commun. 1994, 1205. (c) Hou, Z.; Zhang, Y.; Wakatsuki, Y. Bull. Chem. Soc. Jpn. 1997, 70, 149. (d) Shabangi, M.; Flowers, R. A., II. Tetrahedron Lett. 1997, 38, 1137. (e) Shotwell, J. B.; Sealy, J. M.; Flowers, R. A., II. J. Org. Chem. 1999, 64, 5251. (f) Shabangi, M.; Kuhlman, M. L.; Flowers, R. A., II. Org. Lett. 1999, 1, 2133. (g) Miller, R. S.; Sealy, J. M.; Shabangi, M.; Kuhlman, M. L.; Fuchs, J. R.; Flowers, R. A., II. J. Am. Chem. Soc. 2000, 122, 7718. (h) Prasad, E.; Flowers, R. A., II. J. Am. Chem. Soc. 2002, 124, 6895.
39. 2 is quite understood. See: (a) Hasegawa, E.; Curran, D. P. Tetrahedron Lett. 1993, 34, 1717. (b) Hou, Z.; Wakatsuki, Y. J. Chem. Soc., Chem. Commun. 1994, 1205. (c) Hou, Z.; Zhang, Y.; Wakatsuki, Y. Bull. Chem. Soc. Jpn. 1997, 70, 149. (d) Shabangi, M.; Flowers, R. A., II. Tetrahedron Lett. 1997, 38, 1137. (e) Shotwell, J. B.; Sealy, J. M.; Flowers, R. A., II. J. Org. Chem. 1999, 64, 5251. (f) Shabangi, M.; Kuhlman, M. L.; Flowers, R. A., II. Org. Lett. 1999, 1, 2133. (g) Miller, R. S.; Sealy, J. M.; Shabangi, M.; Kuhlman, M. L.; Fuchs, J. R.; Flowers, R. A., II. J. Am. Chem. Soc. 2000, 122, 7718. (h) Prasad, E.; Flowers, R. A., II. J. Am. Chem. Soc. 2002, 124, 6895.
40. 2 is quite understood. See: (a) Hasegawa, E.; Curran, D. P. Tetrahedron Lett. 1993, 34, 1717. (b) Hou, Z.; Wakatsuki, Y. J. Chem. Soc., Chem. Commun. 1994, 1205. (c) Hou, Z.; Zhang, Y.; Wakatsuki, Y. Bull. Chem. Soc. Jpn. 1997, 70, 149. (d) Shabangi, M.; Flowers, R. A., II. Tetrahedron Lett. 1997, 38, 1137. (e) Shotwell, J. B.; Sealy, J. M.; Flowers, R. A., II. J. Org. Chem. 1999, 64, 5251. (f) Shabangi, M.; Kuhlman, M. L.; Flowers, R. A., II. Org. Lett. 1999, 1, 2133. (g) Miller, R. S.; Sealy, J. M.; Shabangi, M.; Kuhlman, M. L.; Fuchs, J. R.; Flowers, R. A., II. J. Am. Chem. Soc. 2000, 122, 7718. (h) Prasad, E.; Flowers, R. A., II. J. Am. Chem. Soc. 2002, 124, 6895.
41. 2 is quite understood. See: (a) Hasegawa, E.; Curran, D. P. Tetrahedron Lett. 1993, 34, 1717. (b) Hou, Z.; Wakatsuki, Y. J. Chem. Soc., Chem. Commun. 1994, 1205. (c) Hou, Z.; Zhang, Y.; Wakatsuki, Y. Bull. Chem. Soc. Jpn. 1997, 70, 149. (d) Shabangi, M.; Flowers, R. A., II. Tetrahedron Lett. 1997, 38, 1137. (e) Shotwell, J. B.; Sealy, J. M.; Flowers, R. A., II. J. Org. Chem. 1999, 64, 5251. (f) Shabangi, M.; Kuhlman, M. L.; Flowers, R. A., II. Org. Lett. 1999, 1, 2133. (g) Miller, R. S.; Sealy, J. M.; Shabangi, M.; Kuhlman, M. L.; Fuchs, J. R.; Flowers, R. A., II. J. Am. Chem. Soc. 2000, 122, 7718. (h) Prasad, E.; Flowers, R. A., II. J. Am. Chem. Soc. 2002, 124, 6895.
42. 2 is quite understood. See: (a) Hasegawa, E.; Curran, D. P. Tetrahedron Lett. 1993, 34, 1717. (b) Hou, Z.; Wakatsuki, Y. J. Chem. Soc., Chem. Commun. 1994, 1205. (c) Hou, Z.; Zhang, Y.; Wakatsuki, Y. Bull. Chem. Soc. Jpn. 1997, 70, 149. (d) Shabangi, M.; Flowers, R. A., II. Tetrahedron Lett. 1997, 38, 1137. (e) Shotwell, J. B.; Sealy, J. M.; Flowers, R. A., II. J. Org. Chem. 1999, 64, 5251. (f) Shabangi, M.; Kuhlman, M. L.; Flowers, R. A., II. Org. Lett. 1999, 1, 2133. (g) Miller, R. S.; Sealy, J. M.; Shabangi, M.; Kuhlman, M. L.; Fuchs, J. R.; Flowers, R. A., II. J. Am. Chem. Soc. 2000, 122, 7718. (h) Prasad, E.; Flowers, R. A., II. J. Am. Chem. Soc. 2002, 124, 6895.
43. 2 is quite understood. See: (a) Hasegawa, E.; Curran, D. P. Tetrahedron Lett. 1993, 34, 1717. (b) Hou, Z.; Wakatsuki, Y. J. Chem. Soc., Chem. Commun. 1994, 1205. (c) Hou, Z.; Zhang, Y.; Wakatsuki, Y. Bull. Chem. Soc. Jpn. 1997, 70, 149. (d) Shabangi, M.; Flowers, R. A., II. Tetrahedron Lett. 1997, 38, 1137. (e) Shotwell, J. B.; Sealy, J. M.; Flowers, R. A., II. J. Org. Chem. 1999, 64, 5251. (f) Shabangi, M.; Kuhlman, M. L.; Flowers, R. A., II. Org. Lett. 1999, 1, 2133. (g) Miller, R. S.; Sealy, J. M.; Shabangi, M.; Kuhlman, M. L.; Fuchs, J. R.; Flowers, R. A., II. J. Am. Chem. Soc. 2000, 122, 7718. (h) Prasad, E.; Flowers, R. A., II. J. Am. Chem. Soc. 2002, 124, 6895.
44. 2 occurred at the aldehyde group to generate the ketyl-radical intermediate. See: Enholm, E. J.; Trivellas, A. Tetrahedron Lett. 1989, 30, 1063.
45. 2 to the ketone group and the intermolecular pinacol reaction. 9 Then, the single-electron transfer predominantly occurs at the allyl chloride group to form the π-allyl samarium intermediate, and the intramolecular organo-samarium addition reaction exclusively proceeds.
46. 2.
47. 2 in THF.
48. (a) Curran, D. P.; Fevig, T. L.; Jasperse, C. P.; Totleben, M. J. Synlett 1992, 943.
49. (b) Curran, D. P.; Xin, G.; Zhang, W.; Dowd, P. Tetrahedron 1997, 53, 9023.
50. (a) Molander, G. A.; McKie, J. A. J. Org. Chem. 1991, 56, 4112.
51. (b) Batey, R. A.; Motherwell, W. B. Tetrahedron Lett. 1991, 32, 1991.