Reaction of tertiary cyclopropyl silyl ethers with diethylaminosulfur trifluoride: The effects of substituents on the cleavage of the cyclopropane ring

Tetrahedron Letters

Volumn 44, Issue 46, 2003, Pages 8513-8518

  Kirihara, Masayuki ^a   Kakuda, Hiroko ^b   Tsunooka, Makoto ^a   Shimajiri, Akihiro ^a   Takuwa, Tomofumi ^b   Hatano, Akihiko ^a  

^a SHIZUOKA INSTITUTE OF SCIENCE AND TECHNOLOGY   (Japan)

^b UNIVERSITY OF TOYAMA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; CYCLOPROPANE DERIVATIVE; DIETHYLAMINOSULFUR TRIFLUORIDE; ETHER DERIVATIVE; FLUORIDE; SILANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL BOND; CHEMICAL STRUCTURE; ELECTRON; REACTION ANALYSIS; RING OPENING; STRUCTURE ANALYSIS; SUBSTITUTION REACTION;

EID: 0141956452     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.09.089     Document Type: Article

References (36)

1. Reviews: (a) Kuwajima, I.; Nakamura, E. Top. Curr. Chem. 1990, 155, 1-39; (b) Kulinkovich, O. G. Chem. Rev. 2003, 103, 2597-2632.
2. Reviews: (a) Kuwajima, I.; Nakamura, E. Top. Curr. Chem. 1990, 155, 1-39; (b) Kulinkovich, O. G. Chem. Rev. 2003, 103, 2597-2632.
3. Specific 'a'-bond cleavage: (a) Murai, S.; Aya, T.; Renge, T.; Ryu, I.; Sonoda, N. J. Org. Chem. 1974, 39, 858-859; (b) Rubottom G. M.; Lopez, M. I. J. Org. Chem. 1973, 38, 2097-2099; (c) Conia J. M.; Girard, C. Tetrahedron Lett. 1973, 14, 2767-2770; (d) Murai, S.; Seki, Y.; Sonoda, N. J. Chem. Soc. Chem. Commun. 1974, 1032-1033; (e) Ryu, I.; Matsumoto, K.; Ando, M.; Murai, S.; Sonoda, N. Tetrahedron Lett. 1980, 21, 4283-4286; (f) Ryu, I.; Ando, M.; Ogawa, A.; Murai, S.; Sonoda, N. J. Am. Chem. Soc. 1983, 105, 7192-7194; (g) Ryu, I.; Matsumoto, K.; Kameyama, Y.; Ando, M.; Kusumoto, N.; Ogawa, A.; Kambe, N.; Murai, S.; Sonoda, N. J. Am. Chem. Soc. 1993, 115, 12330-12339; (h) Ryu, I.; Murai, S.; Sonoda, N. J. Org. Chem. 1986, 51, 2389-2391; (i) Aoki, S.; Fujimura, T.; Nakamura, E.; Kuwajima, I. J. Am. Chem. Soc. 1988, 110, 3296-3298; (j) Ikura, K.; Ryu, I.; Kambe, N.; Sonoda, N. J. Am. Chem. Soc. 1992, 114, 1520-1521.
4. Specific 'a'-bond cleavage: (a) Murai, S.; Aya, T.; Renge, T.; Ryu, I.; Sonoda, N. J. Org. Chem. 1974, 39, 858-859; (b) Rubottom G. M.; Lopez, M. I. J. Org. Chem. 1973, 38, 2097-2099; (c) Conia J. M.; Girard, C. Tetrahedron Lett. 1973, 14, 2767-2770; (d) Murai, S.; Seki, Y.; Sonoda, N. J. Chem. Soc. Chem. Commun. 1974, 1032-1033; (e) Ryu, I.; Matsumoto, K.; Ando, M.; Murai, S.; Sonoda, N. Tetrahedron Lett. 1980, 21, 4283-4286; (f) Ryu, I.; Ando, M.; Ogawa, A.; Murai, S.; Sonoda, N. J. Am. Chem. Soc. 1983, 105, 7192-7194; (g) Ryu, I.; Matsumoto, K.; Kameyama, Y.; Ando, M.; Kusumoto, N.; Ogawa, A.; Kambe, N.; Murai, S.; Sonoda, N. J. Am. Chem. Soc. 1993, 115, 12330-12339; (h) Ryu, I.; Murai, S.; Sonoda, N. J. Org. Chem. 1986, 51, 2389-2391; (i) Aoki, S.; Fujimura, T.; Nakamura, E.; Kuwajima, I. J. Am. Chem. Soc. 1988, 110, 3296-3298; (j) Ikura, K.; Ryu, I.; Kambe, N.; Sonoda, N. J. Am. Chem. Soc. 1992, 114, 1520-1521.
5. Specific 'a'-bond cleavage: (a) Murai, S.; Aya, T.; Renge, T.; Ryu, I.; Sonoda, N. J. Org. Chem. 1974, 39, 858-859; (b) Rubottom G. M.; Lopez, M. I. J. Org. Chem. 1973, 38, 2097-2099; (c) Conia J. M.; Girard, C. Tetrahedron Lett. 1973, 14, 2767-2770; (d) Murai, S.; Seki, Y.; Sonoda, N. J. Chem. Soc. Chem. Commun. 1974, 1032-1033; (e) Ryu, I.; Matsumoto, K.; Ando, M.; Murai, S.; Sonoda, N. Tetrahedron Lett. 1980, 21, 4283-4286; (f) Ryu, I.; Ando, M.; Ogawa, A.; Murai, S.; Sonoda, N. J. Am. Chem. Soc. 1983, 105, 7192-7194; (g) Ryu, I.; Matsumoto, K.; Kameyama, Y.; Ando, M.; Kusumoto, N.; Ogawa, A.; Kambe, N.; Murai, S.; Sonoda, N. J. Am. Chem. Soc. 1993, 115, 12330-12339; (h) Ryu, I.; Murai, S.; Sonoda, N. J. Org. Chem. 1986, 51, 2389-2391; (i) Aoki, S.; Fujimura, T.; Nakamura, E.; Kuwajima, I. J. Am. Chem. Soc. 1988, 110, 3296-3298; (j) Ikura, K.; Ryu, I.; Kambe, N.; Sonoda, N. J. Am. Chem. Soc. 1992, 114, 1520-1521.
6. Specific 'a'-bond cleavage: (a) Murai, S.; Aya, T.; Renge, T.; Ryu, I.; Sonoda, N. J. Org. Chem. 1974, 39, 858-859; (b) Rubottom G. M.; Lopez, M. I. J. Org. Chem. 1973, 38, 2097-2099; (c) Conia J. M.; Girard, C. Tetrahedron Lett. 1973, 14, 2767-2770; (d) Murai, S.; Seki, Y.; Sonoda, N. J. Chem. Soc. Chem. Commun. 1974, 1032-1033; (e) Ryu, I.; Matsumoto, K.; Ando, M.; Murai, S.; Sonoda, N. Tetrahedron Lett. 1980, 21, 4283-4286; (f) Ryu, I.; Ando, M.; Ogawa, A.; Murai, S.; Sonoda, N. J. Am. Chem. Soc. 1983, 105, 7192-7194; (g) Ryu, I.; Matsumoto, K.; Kameyama, Y.; Ando, M.; Kusumoto, N.; Ogawa, A.; Kambe, N.; Murai, S.; Sonoda, N. J. Am. Chem. Soc. 1993, 115, 12330-12339; (h) Ryu, I.; Murai, S.; Sonoda, N. J. Org. Chem. 1986, 51, 2389-2391; (i) Aoki, S.; Fujimura, T.; Nakamura, E.; Kuwajima, I. J. Am. Chem. Soc. 1988, 110, 3296-3298; (j) Ikura, K.; Ryu, I.; Kambe, N.; Sonoda, N. J. Am. Chem. Soc. 1992, 114, 1520-1521.
7. Specific 'a'-bond cleavage: (a) Murai, S.; Aya, T.; Renge, T.; Ryu, I.; Sonoda, N. J. Org. Chem. 1974, 39, 858-859; (b) Rubottom G. M.; Lopez, M. I. J. Org. Chem. 1973, 38, 2097-2099; (c) Conia J. M.; Girard, C. Tetrahedron Lett. 1973, 14, 2767-2770; (d) Murai, S.; Seki, Y.; Sonoda, N. J. Chem. Soc. Chem. Commun. 1974, 1032-1033; (e) Ryu, I.; Matsumoto, K.; Ando, M.; Murai, S.; Sonoda, N. Tetrahedron Lett. 1980, 21, 4283-4286; (f) Ryu, I.; Ando, M.; Ogawa, A.; Murai, S.; Sonoda, N. J. Am. Chem. Soc. 1983, 105, 7192-7194; (g) Ryu, I.; Matsumoto, K.; Kameyama, Y.; Ando, M.; Kusumoto, N.; Ogawa, A.; Kambe, N.; Murai, S.; Sonoda, N. J. Am. Chem. Soc. 1993, 115, 12330-12339; (h) Ryu, I.; Murai, S.; Sonoda, N. J. Org. Chem. 1986, 51, 2389-2391; (i) Aoki, S.; Fujimura, T.; Nakamura, E.; Kuwajima, I. J. Am. Chem. Soc. 1988, 110, 3296-3298; (j) Ikura, K.; Ryu, I.; Kambe, N.; Sonoda, N. J. Am. Chem. Soc. 1992, 114, 1520-1521.
8. Specific 'a'-bond cleavage: (a) Murai, S.; Aya, T.; Renge, T.; Ryu, I.; Sonoda, N. J. Org. Chem. 1974, 39, 858-859; (b) Rubottom G. M.; Lopez, M. I. J. Org. Chem. 1973, 38, 2097-2099; (c) Conia J. M.; Girard, C. Tetrahedron Lett. 1973, 14, 2767-2770; (d) Murai, S.; Seki, Y.; Sonoda, N. J. Chem. Soc. Chem. Commun. 1974, 1032-1033; (e) Ryu, I.; Matsumoto, K.; Ando, M.; Murai, S.; Sonoda, N. Tetrahedron Lett. 1980, 21, 4283-4286; (f) Ryu, I.; Ando, M.; Ogawa, A.; Murai, S.; Sonoda, N. J. Am. Chem. Soc. 1983, 105, 7192-7194; (g) Ryu, I.; Matsumoto, K.; Kameyama, Y.; Ando, M.; Kusumoto, N.; Ogawa, A.; Kambe, N.; Murai, S.; Sonoda, N. J. Am. Chem. Soc. 1993, 115, 12330-12339; (h) Ryu, I.; Murai, S.; Sonoda, N. J. Org. Chem. 1986, 51, 2389-2391; (i) Aoki, S.; Fujimura, T.; Nakamura, E.; Kuwajima, I. J. Am. Chem. Soc. 1988, 110, 3296-3298; (j) Ikura, K.; Ryu, I.; Kambe, N.; Sonoda, N. J. Am. Chem. Soc. 1992, 114, 1520-1521.
9. Specific 'a'-bond cleavage: (a) Murai, S.; Aya, T.; Renge, T.; Ryu, I.; Sonoda, N. J. Org. Chem. 1974, 39, 858-859; (b) Rubottom G. M.; Lopez, M. I. J. Org. Chem. 1973, 38, 2097-2099; (c) Conia J. M.; Girard, C. Tetrahedron Lett. 1973, 14, 2767-2770; (d) Murai, S.; Seki, Y.; Sonoda, N. J. Chem. Soc. Chem. Commun. 1974, 1032-1033; (e) Ryu, I.; Matsumoto, K.; Ando, M.; Murai, S.; Sonoda, N. Tetrahedron Lett. 1980, 21, 4283-4286; (f) Ryu, I.; Ando, M.; Ogawa, A.; Murai, S.; Sonoda, N. J. Am. Chem. Soc. 1983, 105, 7192-7194; (g) Ryu, I.; Matsumoto, K.; Kameyama, Y.; Ando, M.; Kusumoto, N.; Ogawa, A.; Kambe, N.; Murai, S.; Sonoda, N. J. Am. Chem. Soc. 1993, 115, 12330-12339; (h) Ryu, I.; Murai, S.; Sonoda, N. J. Org. Chem. 1986, 51, 2389-2391; (i) Aoki, S.; Fujimura, T.; Nakamura, E.; Kuwajima, I. J. Am. Chem. Soc. 1988, 110, 3296-3298; (j) Ikura, K.; Ryu, I.; Kambe, N.; Sonoda, N. J. Am. Chem. Soc. 1992, 114, 1520-1521.
10. Specific 'a'-bond cleavage: (a) Murai, S.; Aya, T.; Renge, T.; Ryu, I.; Sonoda, N. J. Org. Chem. 1974, 39, 858-859; (b) Rubottom G. M.; Lopez, M. I. J. Org. Chem. 1973, 38, 2097-2099; (c) Conia J. M.; Girard, C. Tetrahedron Lett. 1973, 14, 2767-2770; (d) Murai, S.; Seki, Y.; Sonoda, N. J. Chem. Soc. Chem. Commun. 1974, 1032-1033; (e) Ryu, I.; Matsumoto, K.; Ando, M.; Murai, S.; Sonoda, N. Tetrahedron Lett. 1980, 21, 4283-4286; (f) Ryu, I.; Ando, M.; Ogawa, A.; Murai, S.; Sonoda, N. J. Am. Chem. Soc. 1983, 105, 7192-7194; (g) Ryu, I.; Matsumoto, K.; Kameyama, Y.; Ando, M.; Kusumoto, N.; Ogawa, A.; Kambe, N.; Murai, S.; Sonoda, N. J. Am. Chem. Soc. 1993, 115, 12330-12339; (h) Ryu, I.; Murai, S.; Sonoda, N. J. Org. Chem. 1986, 51, 2389-2391; (i) Aoki, S.; Fujimura, T.; Nakamura, E.; Kuwajima, I. J. Am. Chem. Soc. 1988, 110, 3296-3298; (j) Ikura, K.; Ryu, I.; Kambe, N.; Sonoda, N. J. Am. Chem. Soc. 1992, 114, 1520-1521.
11. Specific 'a'-bond cleavage: (a) Murai, S.; Aya, T.; Renge, T.; Ryu, I.; Sonoda, N. J. Org. Chem. 1974, 39, 858-859; (b) Rubottom G. M.; Lopez, M. I. J. Org. Chem. 1973, 38, 2097-2099; (c) Conia J. M.; Girard, C. Tetrahedron Lett. 1973, 14, 2767-2770; (d) Murai, S.; Seki, Y.; Sonoda, N. J. Chem. Soc. Chem. Commun. 1974, 1032-1033; (e) Ryu, I.; Matsumoto, K.; Ando, M.; Murai, S.; Sonoda, N. Tetrahedron Lett. 1980, 21, 4283-4286; (f) Ryu, I.; Ando, M.; Ogawa, A.; Murai, S.; Sonoda, N. J. Am. Chem. Soc. 1983, 105, 7192-7194; (g) Ryu, I.; Matsumoto, K.; Kameyama, Y.; Ando, M.; Kusumoto, N.; Ogawa, A.; Kambe, N.; Murai, S.; Sonoda, N. J. Am. Chem. Soc. 1993, 115, 12330-12339; (h) Ryu, I.; Murai, S.; Sonoda, N. J. Org. Chem. 1986, 51, 2389-2391; (i) Aoki, S.; Fujimura, T.; Nakamura, E.; Kuwajima, I. J. Am. Chem. Soc. 1988, 110, 3296-3298; (j) Ikura, K.; Ryu, I.; Kambe, N.; Sonoda, N. J. Am. Chem. Soc. 1992, 114, 1520-1521.
12. Specific 'a'-bond cleavage: (a) Murai, S.; Aya, T.; Renge, T.; Ryu, I.; Sonoda, N. J. Org. Chem. 1974, 39, 858-859; (b) Rubottom G. M.; Lopez, M. I. J. Org. Chem. 1973, 38, 2097-2099; (c) Conia J. M.; Girard, C. Tetrahedron Lett. 1973, 14, 2767-2770; (d) Murai, S.; Seki, Y.; Sonoda, N. J. Chem. Soc. Chem. Commun. 1974, 1032-1033; (e) Ryu, I.; Matsumoto, K.; Ando, M.; Murai, S.; Sonoda, N. Tetrahedron Lett. 1980, 21, 4283-4286; (f) Ryu, I.; Ando, M.; Ogawa, A.; Murai, S.; Sonoda, N. J. Am. Chem. Soc. 1983, 105, 7192-7194; (g) Ryu, I.; Matsumoto, K.; Kameyama, Y.; Ando, M.; Kusumoto, N.; Ogawa, A.; Kambe, N.; Murai, S.; Sonoda, N. J. Am. Chem. Soc. 1993, 115, 12330-12339; (h) Ryu, I.; Murai, S.; Sonoda, N. J. Org. Chem. 1986, 51, 2389-2391; (i) Aoki, S.; Fujimura, T.; Nakamura, E.; Kuwajima, I. J. Am. Chem. Soc. 1988, 110, 3296-3298; (j) Ikura, K.; Ryu, I.; Kambe, N.; Sonoda, N. J. Am. Chem. Soc. 1992, 114, 1520-1521.
13. Specific 'b'-bond cleavage: (a) Ito, Y.; Fujii, S.; Saegusa, T. J. Org. Chem. 1976, 41, 2073-2074; (b) Lewicka-Piekut S.; Okamura, W. H. Synth. Commun. 1980, 10, 415-420; (c) Blanco, L.; Mansouri, A. Tetrahedron Lett. 1988, 29, 3239-3242; (d) Booker-Milburn, K. I. Synlett, 1992, 809-810; (e) Booker-Milburn K. I.; Thompson, D. F. Synlett 1993, 592-594; (f) Torii, S.; Okamoto T.; Ueno, N. J. Chem. Soc. Chem. Commun. 1978, 293-294; (g) Iwasawa, N.; Hayakawa, S.; Isobe, K.; Narasaka, K. Chem. Lett. 1991, 1193-1196; (h) Iwasawa, N.; Funahashi, M.; Hayakawa, S.; Narasaka, K. Chem. Lett. 1993, 545-548; (i) Iwasawa, N.; Hayakawa, S.; Funahashi, M.; Isobe, K.; Narasaka, K. Bull. Chem. Soc. Jpn. 1993, 66, 819-827; (j) Kirihara, M.; Ichinose, M.; Takizawa, S.; Momose, T. Chem. Commun. 1998, 1691-1692.
14. Specific 'b'-bond cleavage: (a) Ito, Y.; Fujii, S.; Saegusa, T. J. Org. Chem. 1976, 41, 2073-2074; (b) Lewicka-Piekut S.; Okamura, W. H. Synth. Commun. 1980, 10, 415-420; (c) Blanco, L.; Mansouri, A. Tetrahedron Lett. 1988, 29, 3239-3242; (d) Booker-Milburn, K. I. Synlett, 1992, 809-810; (e) Booker-Milburn K. I.; Thompson, D. F. Synlett 1993, 592-594; (f) Torii, S.; Okamoto T.; Ueno, N. J. Chem. Soc. Chem. Commun. 1978, 293-294; (g) Iwasawa, N.; Hayakawa, S.; Isobe, K.; Narasaka, K. Chem. Lett. 1991, 1193-1196; (h) Iwasawa, N.; Funahashi, M.; Hayakawa, S.; Narasaka, K. Chem. Lett. 1993, 545-548; (i) Iwasawa, N.; Hayakawa, S.; Funahashi, M.; Isobe, K.; Narasaka, K. Bull. Chem. Soc. Jpn. 1993, 66, 819-827; (j) Kirihara, M.; Ichinose, M.; Takizawa, S.; Momose, T. Chem. Commun. 1998, 1691-1692.
15. Specific 'b'-bond cleavage: (a) Ito, Y.; Fujii, S.; Saegusa, T. J. Org. Chem. 1976, 41, 2073-2074; (b) Lewicka-Piekut S.; Okamura, W. H. Synth. Commun. 1980, 10, 415-420; (c) Blanco, L.; Mansouri, A. Tetrahedron Lett. 1988, 29, 3239-3242; (d) Booker-Milburn, K. I. Synlett, 1992, 809-810; (e) Booker-Milburn K. I.; Thompson, D. F. Synlett 1993, 592-594; (f) Torii, S.; Okamoto T.; Ueno, N. J. Chem. Soc. Chem. Commun. 1978, 293-294; (g) Iwasawa, N.; Hayakawa, S.; Isobe, K.; Narasaka, K. Chem. Lett. 1991, 1193-1196; (h) Iwasawa, N.; Funahashi, M.; Hayakawa, S.; Narasaka, K. Chem. Lett. 1993, 545-548; (i) Iwasawa, N.; Hayakawa, S.; Funahashi, M.; Isobe, K.; Narasaka, K. Bull. Chem. Soc. Jpn. 1993, 66, 819-827; (j) Kirihara, M.; Ichinose, M.; Takizawa, S.; Momose, T. Chem. Commun. 1998, 1691-1692.
16. Specific 'b'-bond cleavage: (a) Ito, Y.; Fujii, S.; Saegusa, T. J. Org. Chem. 1976, 41, 2073-2074; (b) Lewicka-Piekut S.; Okamura, W. H. Synth. Commun. 1980, 10, 415-420; (c) Blanco, L.; Mansouri, A. Tetrahedron Lett. 1988, 29, 3239-3242; (d) Booker-Milburn, K. I. Synlett, 1992, 809-810; (e) Booker-Milburn K. I.; Thompson, D. F. Synlett 1993, 592-594; (f) Torii, S.; Okamoto T.; Ueno, N. J. Chem. Soc. Chem. Commun. 1978, 293-294; (g) Iwasawa, N.; Hayakawa, S.; Isobe, K.; Narasaka, K. Chem. Lett. 1991, 1193-1196; (h) Iwasawa, N.; Funahashi, M.; Hayakawa, S.; Narasaka, K. Chem. Lett. 1993, 545-548; (i) Iwasawa, N.; Hayakawa, S.; Funahashi, M.; Isobe, K.; Narasaka, K. Bull. Chem. Soc. Jpn. 1993, 66, 819-827; (j) Kirihara, M.; Ichinose, M.; Takizawa, S.; Momose, T. Chem. Commun. 1998, 1691-1692.
17. Specific 'b'-bond cleavage: (a) Ito, Y.; Fujii, S.; Saegusa, T. J. Org. Chem. 1976, 41, 2073-2074; (b) Lewicka-Piekut S.; Okamura, W. H. Synth. Commun. 1980, 10, 415-420; (c) Blanco, L.; Mansouri, A. Tetrahedron Lett. 1988, 29, 3239-3242; (d) Booker-Milburn, K. I. Synlett, 1992, 809-810; (e) Booker-Milburn K. I.; Thompson, D. F. Synlett 1993, 592-594; (f) Torii, S.; Okamoto T.; Ueno, N. J. Chem. Soc. Chem. Commun. 1978, 293-294; (g) Iwasawa, N.; Hayakawa, S.; Isobe, K.; Narasaka, K. Chem. Lett. 1991, 1193-1196; (h) Iwasawa, N.; Funahashi, M.; Hayakawa, S.; Narasaka, K. Chem. Lett. 1993, 545-548; (i) Iwasawa, N.; Hayakawa, S.; Funahashi, M.; Isobe, K.; Narasaka, K. Bull. Chem. Soc. Jpn. 1993, 66, 819-827; (j) Kirihara, M.; Ichinose, M.; Takizawa, S.; Momose, T. Chem. Commun. 1998, 1691-1692.
18. Specific 'b'-bond cleavage: (a) Ito, Y.; Fujii, S.; Saegusa, T. J. Org. Chem. 1976, 41, 2073-2074; (b) Lewicka-Piekut S.; Okamura, W. H. Synth. Commun. 1980, 10, 415-420; (c) Blanco, L.; Mansouri, A. Tetrahedron Lett. 1988, 29, 3239-3242; (d) Booker-Milburn, K. I. Synlett, 1992, 809-810; (e) Booker-Milburn K. I.; Thompson, D. F. Synlett 1993, 592-594; (f) Torii, S.; Okamoto T.; Ueno, N. J. Chem. Soc. Chem. Commun. 1978, 293-294; (g) Iwasawa, N.; Hayakawa, S.; Isobe, K.; Narasaka, K. Chem. Lett. 1991, 1193-1196; (h) Iwasawa, N.; Funahashi, M.; Hayakawa, S.; Narasaka, K. Chem. Lett. 1993, 545-548; (i) Iwasawa, N.; Hayakawa, S.; Funahashi, M.; Isobe, K.; Narasaka, K. Bull. Chem. Soc. Jpn. 1993, 66, 819-827; (j) Kirihara, M.; Ichinose, M.; Takizawa, S.; Momose, T. Chem. Commun. 1998, 1691-1692.
19. Specific 'b'-bond cleavage: (a) Ito, Y.; Fujii, S.; Saegusa, T. J. Org. Chem. 1976, 41, 2073-2074; (b) Lewicka-Piekut S.; Okamura, W. H. Synth. Commun. 1980, 10, 415-420; (c) Blanco, L.; Mansouri, A. Tetrahedron Lett. 1988, 29, 3239-3242; (d) Booker-Milburn, K. I. Synlett, 1992, 809-810; (e) Booker-Milburn K. I.; Thompson, D. F. Synlett 1993, 592-594; (f) Torii, S.; Okamoto T.; Ueno, N. J. Chem. Soc. Chem. Commun. 1978, 293-294; (g) Iwasawa, N.; Hayakawa, S.; Isobe, K.; Narasaka, K. Chem. Lett. 1991, 1193-1196; (h) Iwasawa, N.; Funahashi, M.; Hayakawa, S.; Narasaka, K. Chem. Lett. 1993, 545-548; (i) Iwasawa, N.; Hayakawa, S.; Funahashi, M.; Isobe, K.; Narasaka, K. Bull. Chem. Soc. Jpn. 1993, 66, 819-827; (j) Kirihara, M.; Ichinose, M.; Takizawa, S.; Momose, T. Chem. Commun. 1998, 1691-1692.
20. Specific 'b'-bond cleavage: (a) Ito, Y.; Fujii, S.; Saegusa, T. J. Org. Chem. 1976, 41, 2073-2074; (b) Lewicka-Piekut S.; Okamura, W. H. Synth. Commun. 1980, 10, 415-420; (c) Blanco, L.; Mansouri, A. Tetrahedron Lett. 1988, 29, 3239-3242; (d) Booker-Milburn, K. I. Synlett, 1992, 809-810; (e) Booker-Milburn K. I.; Thompson, D. F. Synlett 1993, 592-594; (f) Torii, S.; Okamoto T.; Ueno, N. J. Chem. Soc. Chem. Commun. 1978, 293-294; (g) Iwasawa, N.; Hayakawa, S.; Isobe, K.; Narasaka, K. Chem. Lett. 1991, 1193-1196; (h) Iwasawa, N.; Funahashi, M.; Hayakawa, S.; Narasaka, K. Chem. Lett. 1993, 545-548; (i) Iwasawa, N.; Hayakawa, S.; Funahashi, M.; Isobe, K.; Narasaka, K. Bull. Chem. Soc. Jpn. 1993, 66, 819-827; (j) Kirihara, M.; Ichinose, M.; Takizawa, S.; Momose, T. Chem. Commun. 1998, 1691-1692.
21. Specific 'b'-bond cleavage: (a) Ito, Y.; Fujii, S.; Saegusa, T. J. Org. Chem. 1976, 41, 2073-2074; (b) Lewicka-Piekut S.; Okamura, W. H. Synth. Commun. 1980, 10, 415-420; (c) Blanco, L.; Mansouri, A. Tetrahedron Lett. 1988, 29, 3239-3242; (d) Booker-Milburn, K. I. Synlett, 1992, 809-810; (e) Booker-Milburn K. I.; Thompson, D. F. Synlett 1993, 592-594; (f) Torii, S.; Okamoto T.; Ueno, N. J. Chem. Soc. Chem. Commun. 1978, 293-294; (g) Iwasawa, N.; Hayakawa, S.; Isobe, K.; Narasaka, K. Chem. Lett. 1991, 1193-1196; (h) Iwasawa, N.; Funahashi, M.; Hayakawa, S.; Narasaka, K. Chem. Lett. 1993, 545-548; (i) Iwasawa, N.; Hayakawa, S.; Funahashi, M.; Isobe, K.; Narasaka, K. Bull. Chem. Soc. Jpn. 1993, 66, 819-827; (j) Kirihara, M.; Ichinose, M.; Takizawa, S.; Momose, T. Chem. Commun. 1998, 1691-1692.
22. Specific 'b'-bond cleavage: (a) Ito, Y.; Fujii, S.; Saegusa, T. J. Org. Chem. 1976, 41, 2073-2074; (b) Lewicka-Piekut S.; Okamura, W. H. Synth. Commun. 1980, 10, 415-420; (c) Blanco, L.; Mansouri, A. Tetrahedron Lett. 1988, 29, 3239-3242; (d) Booker-Milburn, K. I. Synlett, 1992, 809-810; (e) Booker-Milburn K. I.; Thompson, D. F. Synlett 1993, 592-594; (f) Torii, S.; Okamoto T.; Ueno, N. J. Chem. Soc. Chem. Commun. 1978, 293-294; (g) Iwasawa, N.; Hayakawa, S.; Isobe, K.; Narasaka, K. Chem. Lett. 1991, 1193-1196; (h) Iwasawa, N.; Funahashi, M.; Hayakawa, S.; Narasaka, K. Chem. Lett. 1993, 545-548; (i) Iwasawa, N.; Hayakawa, S.; Funahashi, M.; Isobe, K.; Narasaka, K. Bull. Chem. Soc. Jpn. 1993, 66, 819-827; (j) Kirihara, M.; Ichinose, M.; Takizawa, S.; Momose, T. Chem. Commun. 1998, 1691-1692.
23. Rubottom G.M., Marrero R., Krueger D.S., Schreiner J.L. Tetrahedron Lett. 1977;4013-4016.
24. Rubottom G.M., Beedle E.C., Kim C.-W., Mott R.C. J. Am. Chem. Soc. 107:1985;4230-4233.
25. Kirihara M., Yokoyama S., Kakuda H., Momose T. Tetrahedron Lett. 36:1995;6907-6910.
26. Kirihara M., Yokoyama S., Momose T. Synth. Commun. 28:1998;1947-1956.
27. Kirihara M., Yokoyama S., Kakuda H., Momose T. Tetrahedron. 54:1998;13943-13954.
28. Momose T., Nishio T., Kirihara M. Tetrahedron Lett. 37:1996;4987-4990.
29. Kirihara M., Nishio T., Yokoyama S., Kakuda H., Momose T. Tetrahedron. 55:1999;2911-2926.
30. Kirihara M., Shimizu M., Yokoyama S., Kakuda H. ITE Lett. 3:2003;215-219.
31. Middleton W.J. J. Org. Chem. 40:1975;574-578 Hudlicky, M. Org. React. (N.Y.) 1988, 35, 513-637; Rock, M. H. In Methods of Organic Chemistry, Workbench Edition; Baasner, B.; Hagemann, H.; Tatlow, J. C., Eds.; Organo-Fluorine Compounds; Thieme: Stuttgart, 2000; Vol. E 10a, pp. 406-431.
32. Middleton W.J. J. Org. Chem. 40:1975;574-578 Hudlicky, M. Org. React. (N.Y.) 1988, 35, 513-637; Rock, M. H. In Methods of Organic Chemistry, Workbench Edition; Baasner, B.; Hagemann, H.; Tatlow, J. C., Eds.; Organo-Fluorine Compounds; Thieme: Stuttgart, 2000; Vol. E 10a, pp. 406-431.
33. Middleton W.J. J. Org. Chem. 40:1975;574-578 Hudlicky, M. Org. React. (N.Y.) 1988, 35, 513-637; Rock, M. H. In Methods of Organic Chemistry, Workbench Edition; Baasner, B.; Hagemann, H.; Tatlow, J. C., Eds.; Organo-Fluorine Compounds; Thieme: Stuttgart, 2000; Vol. E 10a, pp. 406-431.
34. Kirihara M., Kambayashi T., Momose T. Chem. Commun. 1996;1103-1104.
35. Kozyrkov Y.Y., Kulinkovich O.G. Synlett. 2002;443-446.
36. Dolbier W.R. Jr., Battiste M.A. Chem. Rev. 103:2003;1071-1098.