Acyclic selenoiminium salts: Isolation, first structural characterization, and reactions

Organic Letters

Volumn 5, Issue 8, 2003, Pages 1361-1364

  Mutoh, Yuichiro ^a   Murai, Toshiaki ^a  

^a GIFU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

KETONE DERIVATIVE; SELENIUM DERIVATIVE;

AIR; ARTICLE; MOLECULAR DYNAMICS; ROOM TEMPERATURE; X RAY ANALYSIS;

EID: 0141517625     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034334f     Document Type: Article

References (55)

1. For example, see: (a) Shiosaki, K. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, p 865. (b) Mukaiyama, T.; Yamaguchi, T.; Nohira, H. Bull. Chem. Soc. Jpn. 1965, 38, 2107. (c) Mukaiyama, T.; Yamaguchi, T. Bull. Chem. Soc. Jpn. 1966, 39, 2005. (d) Yamaguchi, T.; Inomata, K.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1968, 41, 673. (e) Mathew, S. I.; Stansfield, F. J. Chem. Soc., Perkin Trans. 1 1974, 540. (f) Okecha, S. A.; Stansfield, F. J. Chem. Soc., Perkin Trans. 1 1977, 1811. (g) Shiosaki, K.; Fels, G.; Rapoport, H. J. Org. Chem. 1981, 46, 3230. (h) Sundberg, R. J.; Walters, C. P.; Bloom, J. D. J. Org. Chem. 1981, 46, 3730. (i) Singh, P.; Barata, M. S.; Singh, H. J. Chem. Res., Synop. 1985, 204. (j) Takahata, H.; Yamabe, K.; Yamazaki, T. Synthesis 1986, 1063. (k) Sauve, G.; Mansour, T. S.; Lachance, P.; Belleau, B. Tetrahedron Lett. 1988, 29, 2295. (l) Sauve, G.; Le Berre, N.; Zacharie, B. Tetrahedron Lett. 1988, 29, 2299. (m) Heathcock, C. H.; Davidsen, S. K.; Mills, S. G.; Sanner, M. A. J. Org. Chem. 1992, 57, 2531. (n) Devine, P. N.; Meyers, A. I. J. Am. Chem. Soc. 1994, 116, 2633. (o) Marchand, P.; Fargeau-Bellassoued, M.-C.; Bellec, C.; Lhommet, G. Synthesis 1994, 1118. (p) Mook, R. A., Jr.; Lackey, K.; Bennett, C. Tetrahedron Lett. 1995, 36, 3969. (q) Munchhof, M. J.; Meyers, A. I. J. Am. Chem. Soc. 1995, 117, 5399. (r) Smith, D. C.; Fuchs, P. L. J. Org. Chem. 1995, 60, 2692. (s) Sosnicki, J. G.; Liebscher, J. Synlett 1996, 1117. (t) May, P. J.; Bradley, M.; Harrowven, D. C. ; Pallin, D. Tetrahedron Lett. 2000, 40, 1627.
2. For example, see: (a) Shiosaki, K. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, p 865. (b) Mukaiyama, T.; Yamaguchi, T.; Nohira, H. Bull. Chem. Soc. Jpn. 1965, 38, 2107. (c) Mukaiyama, T.; Yamaguchi, T. Bull. Chem. Soc. Jpn. 1966, 39, 2005. (d) Yamaguchi, T.; Inomata, K.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1968, 41, 673. (e) Mathew, S. I.; Stansfield, F. J. Chem. Soc., Perkin Trans. 1 1974, 540. (f) Okecha, S. A.; Stansfield, F. J. Chem. Soc., Perkin Trans. 1 1977, 1811. (g) Shiosaki, K.; Fels, G.; Rapoport, H. J. Org. Chem. 1981, 46, 3230. (h) Sundberg, R. J.; Walters, C. P.; Bloom, J. D. J. Org. Chem. 1981, 46, 3730. (i) Singh, P.; Barata, M. S.; Singh, H. J. Chem. Res., Synop. 1985, 204. (j) Takahata, H.; Yamabe, K.; Yamazaki, T. Synthesis 1986, 1063. (k) Sauve, G.; Mansour, T. S.; Lachance, P.; Belleau, B. Tetrahedron Lett. 1988, 29, 2295. (l) Sauve, G.; Le Berre, N.; Zacharie, B. Tetrahedron Lett. 1988, 29, 2299. (m) Heathcock, C. H.; Davidsen, S. K.; Mills, S. G.; Sanner, M. A. J. Org. Chem. 1992, 57, 2531. (n) Devine, P. N.; Meyers, A. I. J. Am. Chem. Soc. 1994, 116, 2633. (o) Marchand, P.; Fargeau-Bellassoued, M.-C.; Bellec, C.; Lhommet, G. Synthesis 1994, 1118. (p) Mook, R. A., Jr.; Lackey, K.; Bennett, C. Tetrahedron Lett. 1995, 36, 3969. (q) Munchhof, M. J.; Meyers, A. I. J. Am. Chem. Soc. 1995, 117, 5399. (r) Smith, D. C.; Fuchs, P. L. J. Org. Chem. 1995, 60, 2692. (s) Sosnicki, J. G.; Liebscher, J. Synlett 1996, 1117. (t) May, P. J.; Bradley, M.; Harrowven, D. C. ; Pallin, D. Tetrahedron Lett. 2000, 40, 1627.
3. For example, see: (a) Shiosaki, K. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, p 865. (b) Mukaiyama, T.; Yamaguchi, T.; Nohira, H. Bull. Chem. Soc. Jpn. 1965, 38, 2107. (c) Mukaiyama, T.; Yamaguchi, T. Bull. Chem. Soc. Jpn. 1966, 39, 2005. (d) Yamaguchi, T.; Inomata, K.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1968, 41, 673. (e) Mathew, S. I.; Stansfield, F. J. Chem. Soc., Perkin Trans. 1 1974, 540. (f) Okecha, S. A.; Stansfield, F. J. Chem. Soc., Perkin Trans. 1 1977, 1811. (g) Shiosaki, K.; Fels, G.; Rapoport, H. J. Org. Chem. 1981, 46, 3230. (h) Sundberg, R. J.; Walters, C. P.; Bloom, J. D. J. Org. Chem. 1981, 46, 3730. (i) Singh, P.; Barata, M. S.; Singh, H. J. Chem. Res., Synop. 1985, 204. (j) Takahata, H.; Yamabe, K.; Yamazaki, T. Synthesis 1986, 1063. (k) Sauve, G.; Mansour, T. S.; Lachance, P.; Belleau, B. Tetrahedron Lett. 1988, 29, 2295. (l) Sauve, G.; Le Berre, N.; Zacharie, B. Tetrahedron Lett. 1988, 29, 2299. (m) Heathcock, C. H.; Davidsen, S. K.; Mills, S. G.; Sanner, M. A. J. Org. Chem. 1992, 57, 2531. (n) Devine, P. N.; Meyers, A. I. J. Am. Chem. Soc. 1994, 116, 2633. (o) Marchand, P.; Fargeau-Bellassoued, M.-C.; Bellec, C.; Lhommet, G. Synthesis 1994, 1118. (p) Mook, R. A., Jr.; Lackey, K.; Bennett, C. Tetrahedron Lett. 1995, 36, 3969. (q) Munchhof, M. J.; Meyers, A. I. J. Am. Chem. Soc. 1995, 117, 5399. (r) Smith, D. C.; Fuchs, P. L. J. Org. Chem. 1995, 60, 2692. (s) Sosnicki, J. G.; Liebscher, J. Synlett 1996, 1117. (t) May, P. J.; Bradley, M.; Harrowven, D. C. ; Pallin, D. Tetrahedron Lett. 2000, 40, 1627.
4. For example, see: (a) Shiosaki, K. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, p 865. (b) Mukaiyama, T.; Yamaguchi, T.; Nohira, H. Bull. Chem. Soc. Jpn. 1965, 38, 2107. (c) Mukaiyama, T.; Yamaguchi, T. Bull. Chem. Soc. Jpn. 1966, 39, 2005. (d) Yamaguchi, T.; Inomata, K.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1968, 41, 673. (e) Mathew, S. I.; Stansfield, F. J. Chem. Soc., Perkin Trans. 1 1974, 540. (f) Okecha, S. A.; Stansfield, F. J. Chem. Soc., Perkin Trans. 1 1977, 1811. (g) Shiosaki, K.; Fels, G.; Rapoport, H. J. Org. Chem. 1981, 46, 3230. (h) Sundberg, R. J.; Walters, C. P.; Bloom, J. D. J. Org. Chem. 1981, 46, 3730. (i) Singh, P.; Barata, M. S.; Singh, H. J. Chem. Res., Synop. 1985, 204. (j) Takahata, H.; Yamabe, K.; Yamazaki, T. Synthesis 1986, 1063. (k) Sauve, G.; Mansour, T. S.; Lachance, P.; Belleau, B. Tetrahedron Lett. 1988, 29, 2295. (l) Sauve, G.; Le Berre, N.; Zacharie, B. Tetrahedron Lett. 1988, 29, 2299. (m) Heathcock, C. H.; Davidsen, S. K.; Mills, S. G.; Sanner, M. A. J. Org. Chem. 1992, 57, 2531. (n) Devine, P. N.; Meyers, A. I. J. Am. Chem. Soc. 1994, 116, 2633. (o) Marchand, P.; Fargeau-Bellassoued, M.-C.; Bellec, C.; Lhommet, G. Synthesis 1994, 1118. (p) Mook, R. A., Jr.; Lackey, K.; Bennett, C. Tetrahedron Lett. 1995, 36, 3969. (q) Munchhof, M. J.; Meyers, A. I. J. Am. Chem. Soc. 1995, 117, 5399. (r) Smith, D. C.; Fuchs, P. L. J. Org. Chem. 1995, 60, 2692. (s) Sosnicki, J. G.; Liebscher, J. Synlett 1996, 1117. (t) May, P. J.; Bradley, M.; Harrowven, D. C. ; Pallin, D. Tetrahedron Lett. 2000, 40, 1627.
5. For example, see: (a) Shiosaki, K. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, p 865. (b) Mukaiyama, T.; Yamaguchi, T.; Nohira, H. Bull. Chem. Soc. Jpn. 1965, 38, 2107. (c) Mukaiyama, T.; Yamaguchi, T. Bull. Chem. Soc. Jpn. 1966, 39, 2005. (d) Yamaguchi, T.; Inomata, K.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1968, 41, 673. (e) Mathew, S. I.; Stansfield, F. J. Chem. Soc., Perkin Trans. 1 1974, 540. (f) Okecha, S. A.; Stansfield, F. J. Chem. Soc., Perkin Trans. 1 1977, 1811. (g) Shiosaki, K.; Fels, G.; Rapoport, H. J. Org. Chem. 1981, 46, 3230. (h) Sundberg, R. J.; Walters, C. P.; Bloom, J. D. J. Org. Chem. 1981, 46, 3730. (i) Singh, P.; Barata, M. S.; Singh, H. J. Chem. Res., Synop. 1985, 204. (j) Takahata, H.; Yamabe, K.; Yamazaki, T. Synthesis 1986, 1063. (k) Sauve, G.; Mansour, T. S.; Lachance, P.; Belleau, B. Tetrahedron Lett. 1988, 29, 2295. (l) Sauve, G.; Le Berre, N.; Zacharie, B. Tetrahedron Lett. 1988, 29, 2299. (m) Heathcock, C. H.; Davidsen, S. K.; Mills, S. G.; Sanner, M. A. J. Org. Chem. 1992, 57, 2531. (n) Devine, P. N.; Meyers, A. I. J. Am. Chem. Soc. 1994, 116, 2633. (o) Marchand, P.; Fargeau-Bellassoued, M.-C.; Bellec, C.; Lhommet, G. Synthesis 1994, 1118. (p) Mook, R. A., Jr.; Lackey, K.; Bennett, C. Tetrahedron Lett. 1995, 36, 3969. (q) Munchhof, M. J.; Meyers, A. I. J. Am. Chem. Soc. 1995, 117, 5399. (r) Smith, D. C.; Fuchs, P. L. J. Org. Chem. 1995, 60, 2692. (s) Sosnicki, J. G.; Liebscher, J. Synlett 1996, 1117. (t) May, P. J.; Bradley, M.; Harrowven, D. C. ; Pallin, D. Tetrahedron Lett. 2000, 40, 1627.
6. For example, see: (a) Shiosaki, K. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, p 865. (b) Mukaiyama, T.; Yamaguchi, T.; Nohira, H. Bull. Chem. Soc. Jpn. 1965, 38, 2107. (c) Mukaiyama, T.; Yamaguchi, T. Bull. Chem. Soc. Jpn. 1966, 39, 2005. (d) Yamaguchi, T.; Inomata, K.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1968, 41, 673. (e) Mathew, S. I.; Stansfield, F. J. Chem. Soc., Perkin Trans. 1 1974, 540. (f) Okecha, S. A.; Stansfield, F. J. Chem. Soc., Perkin Trans. 1 1977, 1811. (g) Shiosaki, K.; Fels, G.; Rapoport, H. J. Org. Chem. 1981, 46, 3230. (h) Sundberg, R. J.; Walters, C. P.; Bloom, J. D. J. Org. Chem. 1981, 46, 3730. (i) Singh, P.; Barata, M. S.; Singh, H. J. Chem. Res., Synop. 1985, 204. (j) Takahata, H.; Yamabe, K.; Yamazaki, T. Synthesis 1986, 1063. (k) Sauve, G.; Mansour, T. S.; Lachance, P.; Belleau, B. Tetrahedron Lett. 1988, 29, 2295. (l) Sauve, G.; Le Berre, N.; Zacharie, B. Tetrahedron Lett. 1988, 29, 2299. (m) Heathcock, C. H.; Davidsen, S. K.; Mills, S. G.; Sanner, M. A. J. Org. Chem. 1992, 57, 2531. (n) Devine, P. N.; Meyers, A. I. J. Am. Chem. Soc. 1994, 116, 2633. (o) Marchand, P.; Fargeau-Bellassoued, M.-C.; Bellec, C.; Lhommet, G. Synthesis 1994, 1118. (p) Mook, R. A., Jr.; Lackey, K.; Bennett, C. Tetrahedron Lett. 1995, 36, 3969. (q) Munchhof, M. J.; Meyers, A. I. J. Am. Chem. Soc. 1995, 117, 5399. (r) Smith, D. C.; Fuchs, P. L. J. Org. Chem. 1995, 60, 2692. (s) Sosnicki, J. G.; Liebscher, J. Synlett 1996, 1117. (t) May, P. J.; Bradley, M.; Harrowven, D. C. ; Pallin, D. Tetrahedron Lett. 2000, 40, 1627.
7. For example, see: (a) Shiosaki, K. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, p 865. (b) Mukaiyama, T.; Yamaguchi, T.; Nohira, H. Bull. Chem. Soc. Jpn. 1965, 38, 2107. (c) Mukaiyama, T.; Yamaguchi, T. Bull. Chem. Soc. Jpn. 1966, 39, 2005. (d) Yamaguchi, T.; Inomata, K.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1968, 41, 673. (e) Mathew, S. I.; Stansfield, F. J. Chem. Soc., Perkin Trans. 1 1974, 540. (f) Okecha, S. A.; Stansfield, F. J. Chem. Soc., Perkin Trans. 1 1977, 1811. (g) Shiosaki, K.; Fels, G.; Rapoport, H. J. Org. Chem. 1981, 46, 3230. (h) Sundberg, R. J.; Walters, C. P.; Bloom, J. D. J. Org. Chem. 1981, 46, 3730. (i) Singh, P.; Barata, M. S.; Singh, H. J. Chem. Res., Synop. 1985, 204. (j) Takahata, H.; Yamabe, K.; Yamazaki, T. Synthesis 1986, 1063. (k) Sauve, G.; Mansour, T. S.; Lachance, P.; Belleau, B. Tetrahedron Lett. 1988, 29, 2295. (l) Sauve, G.; Le Berre, N.; Zacharie, B. Tetrahedron Lett. 1988, 29, 2299. (m) Heathcock, C. H.; Davidsen, S. K.; Mills, S. G.; Sanner, M. A. J. Org. Chem. 1992, 57, 2531. (n) Devine, P. N.; Meyers, A. I. J. Am. Chem. Soc. 1994, 116, 2633. (o) Marchand, P.; Fargeau-Bellassoued, M.-C.; Bellec, C.; Lhommet, G. Synthesis 1994, 1118. (p) Mook, R. A., Jr.; Lackey, K.; Bennett, C. Tetrahedron Lett. 1995, 36, 3969. (q) Munchhof, M. J.; Meyers, A. I. J. Am. Chem. Soc. 1995, 117, 5399. (r) Smith, D. C.; Fuchs, P. L. J. Org. Chem. 1995, 60, 2692. (s) Sosnicki, J. G.; Liebscher, J. Synlett 1996, 1117. (t) May, P. J.; Bradley, M.; Harrowven, D. C. ; Pallin, D. Tetrahedron Lett. 2000, 40, 1627.
8. For example, see: (a) Shiosaki, K. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, p 865. (b) Mukaiyama, T.; Yamaguchi, T.; Nohira, H. Bull. Chem. Soc. Jpn. 1965, 38, 2107. (c) Mukaiyama, T.; Yamaguchi, T. Bull. Chem. Soc. Jpn. 1966, 39, 2005. (d) Yamaguchi, T.; Inomata, K.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1968, 41, 673. (e) Mathew, S. I.; Stansfield, F. J. Chem. Soc., Perkin Trans. 1 1974, 540. (f) Okecha, S. A.; Stansfield, F. J. Chem. Soc., Perkin Trans. 1 1977, 1811. (g) Shiosaki, K.; Fels, G.; Rapoport, H. J. Org. Chem. 1981, 46, 3230. (h) Sundberg, R. J.; Walters, C. P.; Bloom, J. D. J. Org. Chem. 1981, 46, 3730. (i) Singh, P.; Barata, M. S.; Singh, H. J. Chem. Res., Synop. 1985, 204. (j) Takahata, H.; Yamabe, K.; Yamazaki, T. Synthesis 1986, 1063. (k) Sauve, G.; Mansour, T. S.; Lachance, P.; Belleau, B. Tetrahedron Lett. 1988, 29, 2295. (l) Sauve, G.; Le Berre, N.; Zacharie, B. Tetrahedron Lett. 1988, 29, 2299. (m) Heathcock, C. H.; Davidsen, S. K.; Mills, S. G.; Sanner, M. A. J. Org. Chem. 1992, 57, 2531. (n) Devine, P. N.; Meyers, A. I. J. Am. Chem. Soc. 1994, 116, 2633. (o) Marchand, P.; Fargeau-Bellassoued, M.-C.; Bellec, C.; Lhommet, G. Synthesis 1994, 1118. (p) Mook, R. A., Jr.; Lackey, K.; Bennett, C. Tetrahedron Lett. 1995, 36, 3969. (q) Munchhof, M. J.; Meyers, A. I. J. Am. Chem. Soc. 1995, 117, 5399. (r) Smith, D. C.; Fuchs, P. L. J. Org. Chem. 1995, 60, 2692. (s) Sosnicki, J. G.; Liebscher, J. Synlett 1996, 1117. (t) May, P. J.; Bradley, M.; Harrowven, D. C. ; Pallin, D. Tetrahedron Lett. 2000, 40, 1627.
9. For example, see: (a) Shiosaki, K. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, p 865. (b) Mukaiyama, T.; Yamaguchi, T.; Nohira, H. Bull. Chem. Soc. Jpn. 1965, 38, 2107. (c) Mukaiyama, T.; Yamaguchi, T. Bull. Chem. Soc. Jpn. 1966, 39, 2005. (d) Yamaguchi, T.; Inomata, K.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1968, 41, 673. (e) Mathew, S. I.; Stansfield, F. J. Chem. Soc., Perkin Trans. 1 1974, 540. (f) Okecha, S. A.; Stansfield, F. J. Chem. Soc., Perkin Trans. 1 1977, 1811. (g) Shiosaki, K.; Fels, G.; Rapoport, H. J. Org. Chem. 1981, 46, 3230. (h) Sundberg, R. J.; Walters, C. P.; Bloom, J. D. J. Org. Chem. 1981, 46, 3730. (i) Singh, P.; Barata, M. S.; Singh, H. J. Chem. Res., Synop. 1985, 204. (j) Takahata, H.; Yamabe, K.; Yamazaki, T. Synthesis 1986, 1063. (k) Sauve, G.; Mansour, T. S.; Lachance, P.; Belleau, B. Tetrahedron Lett. 1988, 29, 2295. (l) Sauve, G.; Le Berre, N.; Zacharie, B. Tetrahedron Lett. 1988, 29, 2299. (m) Heathcock, C. H.; Davidsen, S. K.; Mills, S. G.; Sanner, M. A. J. Org. Chem. 1992, 57, 2531. (n) Devine, P. N.; Meyers, A. I. J. Am. Chem. Soc. 1994, 116, 2633. (o) Marchand, P.; Fargeau-Bellassoued, M.-C.; Bellec, C.; Lhommet, G. Synthesis 1994, 1118. (p) Mook, R. A., Jr.; Lackey, K.; Bennett, C. Tetrahedron Lett. 1995, 36, 3969. (q) Munchhof, M. J.; Meyers, A. I. J. Am. Chem. Soc. 1995, 117, 5399. (r) Smith, D. C.; Fuchs, P. L. J. Org. Chem. 1995, 60, 2692. (s) Sosnicki, J. G.; Liebscher, J. Synlett 1996, 1117. (t) May, P. J.; Bradley, M.; Harrowven, D. C. ; Pallin, D. Tetrahedron Lett. 2000, 40, 1627.
10. For example, see: (a) Shiosaki, K. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, p 865. (b) Mukaiyama, T.; Yamaguchi, T.; Nohira, H. Bull. Chem. Soc. Jpn. 1965, 38, 2107. (c) Mukaiyama, T.; Yamaguchi, T. Bull. Chem. Soc. Jpn. 1966, 39, 2005. (d) Yamaguchi, T.; Inomata, K.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1968, 41, 673. (e) Mathew, S. I.; Stansfield, F. J. Chem. Soc., Perkin Trans. 1 1974, 540. (f) Okecha, S. A.; Stansfield, F. J. Chem. Soc., Perkin Trans. 1 1977, 1811. (g) Shiosaki, K.; Fels, G.; Rapoport, H. J. Org. Chem. 1981, 46, 3230. (h) Sundberg, R. J.; Walters, C. P.; Bloom, J. D. J. Org. Chem. 1981, 46, 3730. (i) Singh, P.; Barata, M. S.; Singh, H. J. Chem. Res., Synop. 1985, 204. (j) Takahata, H.; Yamabe, K.; Yamazaki, T. Synthesis 1986, 1063. (k) Sauve, G.; Mansour, T. S.; Lachance, P.; Belleau, B. Tetrahedron Lett. 1988, 29, 2295. (l) Sauve, G.; Le Berre, N.; Zacharie, B. Tetrahedron Lett. 1988, 29, 2299. (m) Heathcock, C. H.; Davidsen, S. K.; Mills, S. G.; Sanner, M. A. J. Org. Chem. 1992, 57, 2531. (n) Devine, P. N.; Meyers, A. I. J. Am. Chem. Soc. 1994, 116, 2633. (o) Marchand, P.; Fargeau-Bellassoued, M.-C.; Bellec, C.; Lhommet, G. Synthesis 1994, 1118. (p) Mook, R. A., Jr.; Lackey, K.; Bennett, C. Tetrahedron Lett. 1995, 36, 3969. (q) Munchhof, M. J.; Meyers, A. I. J. Am. Chem. Soc. 1995, 117, 5399. (r) Smith, D. C.; Fuchs, P. L. J. Org. Chem. 1995, 60, 2692. (s) Sosnicki, J. G.; Liebscher, J. Synlett 1996, 1117. (t) May, P. J.; Bradley, M.; Harrowven, D. C. ; Pallin, D. Tetrahedron Lett. 2000, 40, 1627.
11. For example, see: (a) Shiosaki, K. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, p 865. (b) Mukaiyama, T.; Yamaguchi, T.; Nohira, H. Bull. Chem. Soc. Jpn. 1965, 38, 2107. (c) Mukaiyama, T.; Yamaguchi, T. Bull. Chem. Soc. Jpn. 1966, 39, 2005. (d) Yamaguchi, T.; Inomata, K.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1968, 41, 673. (e) Mathew, S. I.; Stansfield, F. J. Chem. Soc., Perkin Trans. 1 1974, 540. (f) Okecha, S. A.; Stansfield, F. J. Chem. Soc., Perkin Trans. 1 1977, 1811. (g) Shiosaki, K.; Fels, G.; Rapoport, H. J. Org. Chem. 1981, 46, 3230. (h) Sundberg, R. J.; Walters, C. P.; Bloom, J. D. J. Org. Chem. 1981, 46, 3730. (i) Singh, P.; Barata, M. S.; Singh, H. J. Chem. Res., Synop. 1985, 204. (j) Takahata, H.; Yamabe, K.; Yamazaki, T. Synthesis 1986, 1063. (k) Sauve, G.; Mansour, T. S.; Lachance, P.; Belleau, B. Tetrahedron Lett. 1988, 29, 2295. (l) Sauve, G.; Le Berre, N.; Zacharie, B. Tetrahedron Lett. 1988, 29, 2299. (m) Heathcock, C. H.; Davidsen, S. K.; Mills, S. G.; Sanner, M. A. J. Org. Chem. 1992, 57, 2531. (n) Devine, P. N.; Meyers, A. I. J. Am. Chem. Soc. 1994, 116, 2633. (o) Marchand, P.; Fargeau-Bellassoued, M.-C.; Bellec, C.; Lhommet, G. Synthesis 1994, 1118. (p) Mook, R. A., Jr.; Lackey, K.; Bennett, C. Tetrahedron Lett. 1995, 36, 3969. (q) Munchhof, M. J.; Meyers, A. I. J. Am. Chem. Soc. 1995, 117, 5399. (r) Smith, D. C.; Fuchs, P. L. J. Org. Chem. 1995, 60, 2692. (s) Sosnicki, J. G.; Liebscher, J. Synlett 1996, 1117. (t) May, P. J.; Bradley, M.; Harrowven, D. C. ; Pallin, D. Tetrahedron Lett. 2000, 40, 1627.
12. For example, see: (a) Shiosaki, K. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, p 865. (b) Mukaiyama, T.; Yamaguchi, T.; Nohira, H. Bull. Chem. Soc. Jpn. 1965, 38, 2107. (c) Mukaiyama, T.; Yamaguchi, T. Bull. Chem. Soc. Jpn. 1966, 39, 2005. (d) Yamaguchi, T.; Inomata, K.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1968, 41, 673. (e) Mathew, S. I.; Stansfield, F. J. Chem. Soc., Perkin Trans. 1 1974, 540. (f) Okecha, S. A.; Stansfield, F. J. Chem. Soc., Perkin Trans. 1 1977, 1811. (g) Shiosaki, K.; Fels, G.; Rapoport, H. J. Org. Chem. 1981, 46, 3230. (h) Sundberg, R. J.; Walters, C. P.; Bloom, J. D. J. Org. Chem. 1981, 46, 3730. (i) Singh, P.; Barata, M. S.; Singh, H. J. Chem. Res., Synop. 1985, 204. (j) Takahata, H.; Yamabe, K.; Yamazaki, T. Synthesis 1986, 1063. (k) Sauve, G.; Mansour, T. S.; Lachance, P.; Belleau, B. Tetrahedron Lett. 1988, 29, 2295. (l) Sauve, G.; Le Berre, N.; Zacharie, B. Tetrahedron Lett. 1988, 29, 2299. (m) Heathcock, C. H.; Davidsen, S. K.; Mills, S. G.; Sanner, M. A. J. Org. Chem. 1992, 57, 2531. (n) Devine, P. N.; Meyers, A. I. J. Am. Chem. Soc. 1994, 116, 2633. (o) Marchand, P.; Fargeau-Bellassoued, M.-C.; Bellec, C.; Lhommet, G. Synthesis 1994, 1118. (p) Mook, R. A., Jr.; Lackey, K.; Bennett, C. Tetrahedron Lett. 1995, 36, 3969. (q) Munchhof, M. J.; Meyers, A. I. J. Am. Chem. Soc. 1995, 117, 5399. (r) Smith, D. C.; Fuchs, P. L. J. Org. Chem. 1995, 60, 2692. (s) Sosnicki, J. G.; Liebscher, J. Synlett 1996, 1117. (t) May, P. J.; Bradley, M.; Harrowven, D. C. ; Pallin, D. Tetrahedron Lett. 2000, 40, 1627.
13. For example, see: (a) Shiosaki, K. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, p 865. (b) Mukaiyama, T.; Yamaguchi, T.; Nohira, H. Bull. Chem. Soc. Jpn. 1965, 38, 2107. (c) Mukaiyama, T.; Yamaguchi, T. Bull. Chem. Soc. Jpn. 1966, 39, 2005. (d) Yamaguchi, T.; Inomata, K.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1968, 41, 673. (e) Mathew, S. I.; Stansfield, F. J. Chem. Soc., Perkin Trans. 1 1974, 540. (f) Okecha, S. A.; Stansfield, F. J. Chem. Soc., Perkin Trans. 1 1977, 1811. (g) Shiosaki, K.; Fels, G.; Rapoport, H. J. Org. Chem. 1981, 46, 3230. (h) Sundberg, R. J.; Walters, C. P.; Bloom, J. D. J. Org. Chem. 1981, 46, 3730. (i) Singh, P.; Barata, M. S.; Singh, H. J. Chem. Res., Synop. 1985, 204. (j) Takahata, H.; Yamabe, K.; Yamazaki, T. Synthesis 1986, 1063. (k) Sauve, G.; Mansour, T. S.; Lachance, P.; Belleau, B. Tetrahedron Lett. 1988, 29, 2295. (l) Sauve, G.; Le Berre, N.; Zacharie, B. Tetrahedron Lett. 1988, 29, 2299. (m) Heathcock, C. H.; Davidsen, S. K.; Mills, S. G.; Sanner, M. A. J. Org. Chem. 1992, 57, 2531. (n) Devine, P. N.; Meyers, A. I. J. Am. Chem. Soc. 1994, 116, 2633. (o) Marchand, P.; Fargeau-Bellassoued, M.-C.; Bellec, C.; Lhommet, G. Synthesis 1994, 1118. (p) Mook, R. A., Jr.; Lackey, K.; Bennett, C. Tetrahedron Lett. 1995, 36, 3969. (q) Munchhof, M. J.; Meyers, A. I. J. Am. Chem. Soc. 1995, 117, 5399. (r) Smith, D. C.; Fuchs, P. L. J. Org. Chem. 1995, 60, 2692. (s) Sosnicki, J. G.; Liebscher, J. Synlett 1996, 1117. (t) May, P. J.; Bradley, M.; Harrowven, D. C. ; Pallin, D. Tetrahedron Lett. 2000, 40, 1627.
14. For example, see: (a) Shiosaki, K. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, p 865. (b) Mukaiyama, T.; Yamaguchi, T.; Nohira, H. Bull. Chem. Soc. Jpn. 1965, 38, 2107. (c) Mukaiyama, T.; Yamaguchi, T. Bull. Chem. Soc. Jpn. 1966, 39, 2005. (d) Yamaguchi, T.; Inomata, K.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1968, 41, 673. (e) Mathew, S. I.; Stansfield, F. J. Chem. Soc., Perkin Trans. 1 1974, 540. (f) Okecha, S. A.; Stansfield, F. J. Chem. Soc., Perkin Trans. 1 1977, 1811. (g) Shiosaki, K.; Fels, G.; Rapoport, H. J. Org. Chem. 1981, 46, 3230. (h) Sundberg, R. J.; Walters, C. P.; Bloom, J. D. J. Org. Chem. 1981, 46, 3730. (i) Singh, P.; Barata, M. S.; Singh, H. J. Chem. Res., Synop. 1985, 204. (j) Takahata, H.; Yamabe, K.; Yamazaki, T. Synthesis 1986, 1063. (k) Sauve, G.; Mansour, T. S.; Lachance, P.; Belleau, B. Tetrahedron Lett. 1988, 29, 2295. (l) Sauve, G.; Le Berre, N.; Zacharie, B. Tetrahedron Lett. 1988, 29, 2299. (m) Heathcock, C. H.; Davidsen, S. K.; Mills, S. G.; Sanner, M. A. J. Org. Chem. 1992, 57, 2531. (n) Devine, P. N.; Meyers, A. I. J. Am. Chem. Soc. 1994, 116, 2633. (o) Marchand, P.; Fargeau-Bellassoued, M.-C.; Bellec, C.; Lhommet, G. Synthesis 1994, 1118. (p) Mook, R. A., Jr.; Lackey, K.; Bennett, C. Tetrahedron Lett. 1995, 36, 3969. (q) Munchhof, M. J.; Meyers, A. I. J. Am. Chem. Soc. 1995, 117, 5399. (r) Smith, D. C.; Fuchs, P. L. J. Org. Chem. 1995, 60, 2692. (s) Sosnicki, J. G.; Liebscher, J. Synlett 1996, 1117. (t) May, P. J.; Bradley, M.; Harrowven, D. C. ; Pallin, D. Tetrahedron Lett. 2000, 40, 1627.
15. For example, see: (a) Shiosaki, K. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, p 865. (b) Mukaiyama, T.; Yamaguchi, T.; Nohira, H. Bull. Chem. Soc. Jpn. 1965, 38, 2107. (c) Mukaiyama, T.; Yamaguchi, T. Bull. Chem. Soc. Jpn. 1966, 39, 2005. (d) Yamaguchi, T.; Inomata, K.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1968, 41, 673. (e) Mathew, S. I.; Stansfield, F. J. Chem. Soc., Perkin Trans. 1 1974, 540. (f) Okecha, S. A.; Stansfield, F. J. Chem. Soc., Perkin Trans. 1 1977, 1811. (g) Shiosaki, K.; Fels, G.; Rapoport, H. J. Org. Chem. 1981, 46, 3230. (h) Sundberg, R. J.; Walters, C. P.; Bloom, J. D. J. Org. Chem. 1981, 46, 3730. (i) Singh, P.; Barata, M. S.; Singh, H. J. Chem. Res., Synop. 1985, 204. (j) Takahata, H.; Yamabe, K.; Yamazaki, T. Synthesis 1986, 1063. (k) Sauve, G.; Mansour, T. S.; Lachance, P.; Belleau, B. Tetrahedron Lett. 1988, 29, 2295. (l) Sauve, G.; Le Berre, N.; Zacharie, B. Tetrahedron Lett. 1988, 29, 2299. (m) Heathcock, C. H.; Davidsen, S. K.; Mills, S. G.; Sanner, M. A. J. Org. Chem. 1992, 57, 2531. (n) Devine, P. N.; Meyers, A. I. J. Am. Chem. Soc. 1994, 116, 2633. (o) Marchand, P.; Fargeau-Bellassoued, M.-C.; Bellec, C.; Lhommet, G. Synthesis 1994, 1118. (p) Mook, R. A., Jr.; Lackey, K.; Bennett, C. Tetrahedron Lett. 1995, 36, 3969. (q) Munchhof, M. J.; Meyers, A. I. J. Am. Chem. Soc. 1995, 117, 5399. (r) Smith, D. C.; Fuchs, P. L. J. Org. Chem. 1995, 60, 2692. (s) Sosnicki, J. G.; Liebscher, J. Synlett 1996, 1117. (t) May, P. J.; Bradley, M.; Harrowven, D. C. ; Pallin, D. Tetrahedron Lett. 2000, 40, 1627.
16. For example, see: (a) Shiosaki, K. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, p 865. (b) Mukaiyama, T.; Yamaguchi, T.; Nohira, H. Bull. Chem. Soc. Jpn. 1965, 38, 2107. (c) Mukaiyama, T.; Yamaguchi, T. Bull. Chem. Soc. Jpn. 1966, 39, 2005. (d) Yamaguchi, T.; Inomata, K.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1968, 41, 673. (e) Mathew, S. I.; Stansfield, F. J. Chem. Soc., Perkin Trans. 1 1974, 540. (f) Okecha, S. A.; Stansfield, F. J. Chem. Soc., Perkin Trans. 1 1977, 1811. (g) Shiosaki, K.; Fels, G.; Rapoport, H. J. Org. Chem. 1981, 46, 3230. (h) Sundberg, R. J.; Walters, C. P.; Bloom, J. D. J. Org. Chem. 1981, 46, 3730. (i) Singh, P.; Barata, M. S.; Singh, H. J. Chem. Res., Synop. 1985, 204. (j) Takahata, H.; Yamabe, K.; Yamazaki, T. Synthesis 1986, 1063. (k) Sauve, G.; Mansour, T. S.; Lachance, P.; Belleau, B. Tetrahedron Lett. 1988, 29, 2295. (l) Sauve, G.; Le Berre, N.; Zacharie, B. Tetrahedron Lett. 1988, 29, 2299. (m) Heathcock, C. H.; Davidsen, S. K.; Mills, S. G.; Sanner, M. A. J. Org. Chem. 1992, 57, 2531. (n) Devine, P. N.; Meyers, A. I. J. Am. Chem. Soc. 1994, 116, 2633. (o) Marchand, P.; Fargeau-Bellassoued, M.-C.; Bellec, C.; Lhommet, G. Synthesis 1994, 1118. (p) Mook, R. A., Jr.; Lackey, K.; Bennett, C. Tetrahedron Lett. 1995, 36, 3969. (q) Munchhof, M. J.; Meyers, A. I. J. Am. Chem. Soc. 1995, 117, 5399. (r) Smith, D. C.; Fuchs, P. L. J. Org. Chem. 1995, 60, 2692. (s) Sosnicki, J. G.; Liebscher, J. Synlett 1996, 1117. (t) May, P. J.; Bradley, M.; Harrowven, D. C. ; Pallin, D. Tetrahedron Lett. 2000, 40, 1627.
17. For example, see: (a) Shiosaki, K. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, p 865. (b) Mukaiyama, T.; Yamaguchi, T.; Nohira, H. Bull. Chem. Soc. Jpn. 1965, 38, 2107. (c) Mukaiyama, T.; Yamaguchi, T. Bull. Chem. Soc. Jpn. 1966, 39, 2005. (d) Yamaguchi, T.; Inomata, K.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1968, 41, 673. (e) Mathew, S. I.; Stansfield, F. J. Chem. Soc., Perkin Trans. 1 1974, 540. (f) Okecha, S. A.; Stansfield, F. J. Chem. Soc., Perkin Trans. 1 1977, 1811. (g) Shiosaki, K.; Fels, G.; Rapoport, H. J. Org. Chem. 1981, 46, 3230. (h) Sundberg, R. J.; Walters, C. P.; Bloom, J. D. J. Org. Chem. 1981, 46, 3730. (i) Singh, P.; Barata, M. S.; Singh, H. J. Chem. Res., Synop. 1985, 204. (j) Takahata, H.; Yamabe, K.; Yamazaki, T. Synthesis 1986, 1063. (k) Sauve, G.; Mansour, T. S.; Lachance, P.; Belleau, B. Tetrahedron Lett. 1988, 29, 2295. (l) Sauve, G.; Le Berre, N.; Zacharie, B. Tetrahedron Lett. 1988, 29, 2299. (m) Heathcock, C. H.; Davidsen, S. K.; Mills, S. G.; Sanner, M. A. J. Org. Chem. 1992, 57, 2531. (n) Devine, P. N.; Meyers, A. I. J. Am. Chem. Soc. 1994, 116, 2633. (o) Marchand, P.; Fargeau-Bellassoued, M.-C.; Bellec, C.; Lhommet, G. Synthesis 1994, 1118. (p) Mook, R. A., Jr.; Lackey, K.; Bennett, C. Tetrahedron Lett. 1995, 36, 3969. (q) Munchhof, M. J.; Meyers, A. I. J. Am. Chem. Soc. 1995, 117, 5399. (r) Smith, D. C.; Fuchs, P. L. J. Org. Chem. 1995, 60, 2692. (s) Sosnicki, J. G.; Liebscher, J. Synlett 1996, 1117. (t) May, P. J.; Bradley, M.; Harrowven, D. C. ; Pallin, D. Tetrahedron Lett. 2000, 40, 1627.
18. For example, see: (a) Shiosaki, K. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, p 865. (b) Mukaiyama, T.; Yamaguchi, T.; Nohira, H. Bull. Chem. Soc. Jpn. 1965, 38, 2107. (c) Mukaiyama, T.; Yamaguchi, T. Bull. Chem. Soc. Jpn. 1966, 39, 2005. (d) Yamaguchi, T.; Inomata, K.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1968, 41, 673. (e) Mathew, S. I.; Stansfield, F. J. Chem. Soc., Perkin Trans. 1 1974, 540. (f) Okecha, S. A.; Stansfield, F. J. Chem. Soc., Perkin Trans. 1 1977, 1811. (g) Shiosaki, K.; Fels, G.; Rapoport, H. J. Org. Chem. 1981, 46, 3230. (h) Sundberg, R. J.; Walters, C. P.; Bloom, J. D. J. Org. Chem. 1981, 46, 3730. (i) Singh, P.; Barata, M. S.; Singh, H. J. Chem. Res., Synop. 1985, 204. (j) Takahata, H.; Yamabe, K.; Yamazaki, T. Synthesis 1986, 1063. (k) Sauve, G.; Mansour, T. S.; Lachance, P.; Belleau, B. Tetrahedron Lett. 1988, 29, 2295. (l) Sauve, G.; Le Berre, N.; Zacharie, B. Tetrahedron Lett. 1988, 29, 2299. (m) Heathcock, C. H.; Davidsen, S. K.; Mills, S. G.; Sanner, M. A. J. Org. Chem. 1992, 57, 2531. (n) Devine, P. N.; Meyers, A. I. J. Am. Chem. Soc. 1994, 116, 2633. (o) Marchand, P.; Fargeau-Bellassoued, M.-C.; Bellec, C.; Lhommet, G. Synthesis 1994, 1118. (p) Mook, R. A., Jr.; Lackey, K.; Bennett, C. Tetrahedron Lett. 1995, 36, 3969. (q) Munchhof, M. J.; Meyers, A. I. J. Am. Chem. Soc. 1995, 117, 5399. (r) Smith, D. C.; Fuchs, P. L. J. Org. Chem. 1995, 60, 2692. (s) Sosnicki, J. G.; Liebscher, J. Synlett 1996, 1117. (t) May, P. J.; Bradley, M.; Harrowven, D. C. ; Pallin, D. Tetrahedron Lett. 2000, 40, 1627.
19. For example, see: (a) Shiosaki, K. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, p 865. (b) Mukaiyama, T.; Yamaguchi, T.; Nohira, H. Bull. Chem. Soc. Jpn. 1965, 38, 2107. (c) Mukaiyama, T.; Yamaguchi, T. Bull. Chem. Soc. Jpn. 1966, 39, 2005. (d) Yamaguchi, T.; Inomata, K.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1968, 41, 673. (e) Mathew, S. I.; Stansfield, F. J. Chem. Soc., Perkin Trans. 1 1974, 540. (f) Okecha, S. A.; Stansfield, F. J. Chem. Soc., Perkin Trans. 1 1977, 1811. (g) Shiosaki, K.; Fels, G.; Rapoport, H. J. Org. Chem. 1981, 46, 3230. (h) Sundberg, R. J.; Walters, C. P.; Bloom, J. D. J. Org. Chem. 1981, 46, 3730. (i) Singh, P.; Barata, M. S.; Singh, H. J. Chem. Res., Synop. 1985, 204. (j) Takahata, H.; Yamabe, K.; Yamazaki, T. Synthesis 1986, 1063. (k) Sauve, G.; Mansour, T. S.; Lachance, P.; Belleau, B. Tetrahedron Lett. 1988, 29, 2295. (l) Sauve, G.; Le Berre, N.; Zacharie, B. Tetrahedron Lett. 1988, 29, 2299. (m) Heathcock, C. H.; Davidsen, S. K.; Mills, S. G.; Sanner, M. A. J. Org. Chem. 1992, 57, 2531. (n) Devine, P. N.; Meyers, A. I. J. Am. Chem. Soc. 1994, 116, 2633. (o) Marchand, P.; Fargeau-Bellassoued, M.-C.; Bellec, C.; Lhommet, G. Synthesis 1994, 1118. (p) Mook, R. A., Jr.; Lackey, K.; Bennett, C. Tetrahedron Lett. 1995, 36, 3969. (q) Munchhof, M. J.; Meyers, A. I. J. Am. Chem. Soc. 1995, 117, 5399. (r) Smith, D. C.; Fuchs, P. L. J. Org. Chem. 1995, 60, 2692. (s) Sosnicki, J. G.; Liebscher, J. Synlett 1996, 1117. (t) May, P. J.; Bradley, M.; Harrowven, D. C. ; Pallin, D. Tetrahedron Lett. 2000, 40, 1627.
20. For example, see: (a) Shiosaki, K. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, p 865. (b) Mukaiyama, T.; Yamaguchi, T.; Nohira, H. Bull. Chem. Soc. Jpn. 1965, 38, 2107. (c) Mukaiyama, T.; Yamaguchi, T. Bull. Chem. Soc. Jpn. 1966, 39, 2005. (d) Yamaguchi, T.; Inomata, K.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1968, 41, 673. (e) Mathew, S. I.; Stansfield, F. J. Chem. Soc., Perkin Trans. 1 1974, 540. (f) Okecha, S. A.; Stansfield, F. J. Chem. Soc., Perkin Trans. 1 1977, 1811. (g) Shiosaki, K.; Fels, G.; Rapoport, H. J. Org. Chem. 1981, 46, 3230. (h) Sundberg, R. J.; Walters, C. P.; Bloom, J. D. J. Org. Chem. 1981, 46, 3730. (i) Singh, P.; Barata, M. S.; Singh, H. J. Chem. Res., Synop. 1985, 204. (j) Takahata, H.; Yamabe, K.; Yamazaki, T. Synthesis 1986, 1063. (k) Sauve, G.; Mansour, T. S.; Lachance, P.; Belleau, B. Tetrahedron Lett. 1988, 29, 2295. (l) Sauve, G.; Le Berre, N.; Zacharie, B. Tetrahedron Lett. 1988, 29, 2299. (m) Heathcock, C. H.; Davidsen, S. K.; Mills, S. G.; Sanner, M. A. J. Org. Chem. 1992, 57, 2531. (n) Devine, P. N.; Meyers, A. I. J. Am. Chem. Soc. 1994, 116, 2633. (o) Marchand, P.; Fargeau-Bellassoued, M.-C.; Bellec, C.; Lhommet, G. Synthesis 1994, 1118. (p) Mook, R. A., Jr.; Lackey, K.; Bennett, C. Tetrahedron Lett. 1995, 36, 3969. (q) Munchhof, M. J.; Meyers, A. I. J. Am. Chem. Soc. 1995, 117, 5399. (r) Smith, D. C.; Fuchs, P. L. J. Org. Chem. 1995, 60, 2692. (s) Sosnicki, J. G.; Liebscher, J. Synlett 1996, 1117. (t) May, P. J.; Bradley, M.; Harrowven, D. C. ; Pallin, D. Tetrahedron Lett. 2000, 40, 1627.
21. Jensen and Nielsen reported the synthesis of selenoiminium salts by reacting selenoacetamide, selenobenzamide, selenoformamide, and selenoureas with methyl iodide: Jensen, K. A.; Nielsen, P. H. Acta Chem. Scand. 1966, 20, 597.
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39. For example, see: (a) Cohen, V. I. J. Org. Chem. 1977, 42, 2645. (b) Blau, H.; Grobe, J.; Le Van, D.; Krebs, B.; Läge, M. Chem. Ber. 1997, 130, 913. (c) Ishihara, H.; Koketsu, M.; Fukuta, Y.; Nada, F. J. Am. Chem. Soc. 2001, 123, 8408. (d) Koketsu, M.; Kanoh, M.; Itoh, E.; Ishihara, H. J. Org. Chem. 2001, 66, 4099. (e) Bhattacharyya, P.; Woollins, J. D. Tetrahedron Lett. 2001, 42, 5949. (f) Koketsu, M.; Okayama, Y.; Aoki, H.; Ishihara, H. Heteroatom Chem. 2002, 13, 195.
40. For example, see: (a) Cohen, V. I. J. Org. Chem. 1977, 42, 2645. (b) Blau, H.; Grobe, J.; Le Van, D.; Krebs, B.; Läge, M. Chem. Ber. 1997, 130, 913. (c) Ishihara, H.; Koketsu, M.; Fukuta, Y.; Nada, F. J. Am. Chem. Soc. 2001, 123, 8408. (d) Koketsu, M.; Kanoh, M.; Itoh, E.; Ishihara, H. J. Org. Chem. 2001, 66, 4099. (e) Bhattacharyya, P.; Woollins, J. D. Tetrahedron Lett. 2001, 42, 5949. (f) Koketsu, M.; Okayama, Y.; Aoki, H.; Ishihara, H. Heteroatom Chem. 2002, 13, 195.
41. For example, see: (a) Cohen, V. I. J. Org. Chem. 1977, 42, 2645. (b) Blau, H.; Grobe, J.; Le Van, D.; Krebs, B.; Läge, M. Chem. Ber. 1997, 130, 913. (c) Ishihara, H.; Koketsu, M.; Fukuta, Y.; Nada, F. J. Am. Chem. Soc. 2001, 123, 8408. (d) Koketsu, M.; Kanoh, M.; Itoh, E.; Ishihara, H. J. Org. Chem. 2001, 66, 4099. (e) Bhattacharyya, P.; Woollins, J. D. Tetrahedron Lett. 2001, 42, 5949. (f) Koketsu, M.; Okayama, Y.; Aoki, H.; Ishihara, H. Heteroatom Chem. 2002, 13, 195.
42. For example, see: (a) Cohen, V. I. J. Org. Chem. 1977, 42, 2645. (b) Blau, H.; Grobe, J.; Le Van, D.; Krebs, B.; Läge, M. Chem. Ber. 1997, 130, 913. (c) Ishihara, H.; Koketsu, M.; Fukuta, Y.; Nada, F. J. Am. Chem. Soc. 2001, 123, 8408. (d) Koketsu, M.; Kanoh, M.; Itoh, E.; Ishihara, H. J. Org. Chem. 2001, 66, 4099. (e) Bhattacharyya, P.; Woollins, J. D. Tetrahedron Lett. 2001, 42, 5949. (f) Koketsu, M.; Okayama, Y.; Aoki, H.; Ishihara, H. Heteroatom Chem. 2002, 13, 195.
43. For example, see: (a) Cohen, V. I. J. Org. Chem. 1977, 42, 2645. (b) Blau, H.; Grobe, J.; Le Van, D.; Krebs, B.; Läge, M. Chem. Ber. 1997, 130, 913. (c) Ishihara, H.; Koketsu, M.; Fukuta, Y.; Nada, F. J. Am. Chem. Soc. 2001, 123, 8408. (d) Koketsu, M.; Kanoh, M.; Itoh, E.; Ishihara, H. J. Org. Chem. 2001, 66, 4099. (e) Bhattacharyya, P.; Woollins, J. D. Tetrahedron Lett. 2001, 42, 5949. (f) Koketsu, M.; Okayama, Y.; Aoki, H.; Ishihara, H. Heteroatom Chem. 2002, 13, 195.
44. For example, see: (a) Cohen, V. I. J. Org. Chem. 1977, 42, 2645. (b) Blau, H.; Grobe, J.; Le Van, D.; Krebs, B.; Läge, M. Chem. Ber. 1997, 130, 913. (c) Ishihara, H.; Koketsu, M.; Fukuta, Y.; Nada, F. J. Am. Chem. Soc. 2001, 123, 8408. (d) Koketsu, M.; Kanoh, M.; Itoh, E.; Ishihara, H. J. Org. Chem. 2001, 66, 4099. (e) Bhattacharyya, P.; Woollins, J. D. Tetrahedron Lett. 2001, 42, 5949. (f) Koketsu, M.; Okayama, Y.; Aoki, H.; Ishihara, H. Heteroatom Chem. 2002, 13, 195.
45. 3SSe: C, 35.11; H, 3.75. Found: C, 35.40; H, 3.77.
46. Stereochemistry was determined by phase-sensitive NOESY spectroscopy.
47. I = 0.047, 3395 reflections (I > -10.00σ(I)), GOF = 1.08.
48. Katritzky, A. R.; Qi, M. J. Org. Chem. 1997, 62, 4116.
49. These pathways were suggested by the fact that butyl methyl selenide (BuSeMe) and dimethyl diselenide (MeSeSeMe) were detected as byproducts.
50. Synthesis and isolation of tellurobenzamide and telluroformamides have been reported: (a) Lerstrup, K. A.; Henriksen, L. J. Chem. Soc., Chem. Commun. 1979, 1102. (b) Segi, M.; Kojima, A.; Nakajama, T.; Suga, S. Synlett 1991, 105. (c) Li, G. M.; Zingaro, R. A.; Segi, M.; Reibenspies, J. H.; Nakajima, T. Organometallics 1997, 16, 756. (d) Li, G. M.; Zingaro, R. A. J. Chem. Soc., Perkin Trans. 1 1998, 647.
51. Synthesis and isolation of tellurobenzamide and telluroformamides have been reported: (a) Lerstrup, K. A.; Henriksen, L. J. Chem. Soc., Chem. Commun. 1979, 1102. (b) Segi, M.; Kojima, A.; Nakajama, T.; Suga, S. Synlett 1991, 105. (c) Li, G. M.; Zingaro, R. A.; Segi, M.; Reibenspies, J. H.; Nakajima, T. Organometallics 1997, 16, 756. (d) Li, G. M.; Zingaro, R. A. J. Chem. Soc., Perkin Trans. 1 1998, 647.
52. Synthesis and isolation of tellurobenzamide and telluroformamides have been reported: (a) Lerstrup, K. A.; Henriksen, L. J. Chem. Soc., Chem. Commun. 1979, 1102. (b) Segi, M.; Kojima, A.; Nakajama, T.; Suga, S. Synlett 1991, 105. (c) Li, G. M.; Zingaro, R. A.; Segi, M.; Reibenspies, J. H.; Nakajima, T. Organometallics 1997, 16, 756. (d) Li, G. M.; Zingaro, R. A. J. Chem. Soc., Perkin Trans. 1 1998, 647.
53. Synthesis and isolation of tellurobenzamide and telluroformamides have been reported: (a) Lerstrup, K. A.; Henriksen, L. J. Chem. Soc., Chem. Commun. 1979, 1102. (b) Segi, M.; Kojima, A.; Nakajama, T.; Suga, S. Synlett 1991, 105. (c) Li, G. M.; Zingaro, R. A.; Segi, M.; Reibenspies, J. H.; Nakajima, T. Organometallics 1997, 16, 756. (d) Li, G. M.; Zingaro, R. A. J. Chem. Soc., Perkin Trans. 1 1998, 647.
54. Attempts to isolate aliphatic telluroamides have been reported to give decomposed products: Laishev, V. Z.; Petrov, M. L.; Petrov, A. A. Zh. Org. Khim. 1981, 17, 2064.
55. 17-NTe 317.0423, found 317.0420.