Diastereo-differentiation during 2,4-pentanediol tethered simmons-smith type cyclopropanation: Reaction species of hydroxyl group directed zinc carbenoid addition

Chemistry Letters

Volumn , Issue 8, 1999, Pages 831-832

  Sugimura, Takashi ^a   Yoshikawa, Masato ^a   Mizuguchi, Miki ^a   Tai, Akira ^a  

^a UNIVERSITY OF HYOGO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0033245584     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1999.831     Document Type: Article

References (17)

1. For reviews, see: T. Sugimura, J. Synth. Org. Chem. Jpn., 55, 517 (1997). T. Sugimura, in "Recent Research Developments in Organic Chemistry," ed by S. G. Pandalai, Transworld Research Network, India (1998), 3, p. 47.
2. For reviews, see: T. Sugimura, J. Synth. Org. Chem. Jpn., 55, 517 (1997). T. Sugimura, in "Recent Research Developments in Organic Chemistry," ed by S. G. Pandalai, Transworld Research Network, India (1998), 3, p. 47.
3. a) T. Sugimura, T. Futagawa, and A. Tai, Tetrahedron Lett., 29, 5775 (1988).
4. b) T. Sugimura, M. Yoshikawa, T. Futagawa, and A. Tai, Tetrahedron, 46, 5955 (1990);
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6. T. Sugimura, N. Nishiyama, and A. Tai, Tetrahedron: Asymmetry, 4, 43 (1993). T. Sugimura, H. Iguchi, R. Tsuchida, A. Tai, N. Nishiyama, and T. Hakushi, Tetrahedron: Asymmetry, 9, 1007 (1998).
7. For general discussions for the structure of zinc carbenoids, see: E. P. Blanchard and H. E. Simmons, J. Am. Chem. Soc., 86, 1337 (1964). H. E. Simmons, Org. React., 20, 1 (1973). J. Furukawa and N. Kawabata, in "Advances in Organometallic Chemistry," ed by F. G. A. Stone and R. West, Academic Press, New York (1974), 12, p. 83. J. Boersma, in "Comprehensive Organometallic Chemistry," ed by G. Wilkinson, Pergamon Press, New York (1982) p. 823.
8. For general discussions for the structure of zinc carbenoids, see: E. P. Blanchard and H. E. Simmons, J. Am. Chem. Soc., 86, 1337 (1964). H. E. Simmons, Org. React., 20, 1 (1973). J. Furukawa and N. Kawabata, in "Advances in Organometallic Chemistry," ed by F. G. A. Stone and R. West, Academic Press, New York (1974), 12, p. 83. J. Boersma, in "Comprehensive Organometallic Chemistry," ed by G. Wilkinson, Pergamon Press, New York (1982) p. 823.
9. For general discussions for the structure of zinc carbenoids, see: E. P. Blanchard and H. E. Simmons, J. Am. Chem. Soc., 86, 1337 (1964). H. E. Simmons, Org. React., 20, 1 (1973). J. Furukawa and N. Kawabata, in "Advances in Organometallic Chemistry," ed by F. G. A. Stone and R. West, Academic Press, New York (1974), 12, p. 83. J. Boersma, in "Comprehensive Organometallic Chemistry," ed by G. Wilkinson, Pergamon Press, New York (1982) p. 823.
10. For general discussions for the structure of zinc carbenoids, see: E. P. Blanchard and H. E. Simmons, J. Am. Chem. Soc., 86, 1337 (1964). H. E. Simmons, Org. React., 20, 1 (1973). J. Furukawa and N. Kawabata, in "Advances in Organometallic Chemistry," ed by F. G. A. Stone and R. West, Academic Press, New York (1974), 12, p. 83. J. Boersma, in "Comprehensive Organometallic Chemistry," ed by G. Wilkinson, Pergamon Press, New York (1982) p. 823.
11. J. H. H-. Chan and B. Richkborn, J. Am. Chem. Soc., 90, 6406 (1968). N. Kawabata, T. Nakagawa, T. Nakao, and S. Yamashita, J. Org. Chem., 42, 3031 (1977). S. E. Denmark, J. P. Edward, and S. R. Wilson, J. Am. Chem. Soc., 114, 2592 (1992). A. B. Charette and C. Brochu, J. Am. Chem. Soc., 117, 11367 (1995). A. B. Charette and J. -F. Marcoux, J. Am. Chem. Soc., 118, 4539 (1996). S. E. Denmark and S. P. O'Connor, J. Org. Chem., 62, 3390 (1997). H. Takahashi, M. Yoshioka, M. Ohno, and S. Kobayashi, Tetrahedron Lett., 33, 2575 (1997).
12. J. H. H-. Chan and B. Richkborn, J. Am. Chem. Soc., 90, 6406 (1968). N. Kawabata, T. Nakagawa, T. Nakao, and S. Yamashita, J. Org. Chem., 42, 3031 (1977). S. E. Denmark, J. P. Edward, and S. R. Wilson, J. Am. Chem. Soc., 114, 2592 (1992). A. B. Charette and C. Brochu, J. Am. Chem. Soc., 117, 11367 (1995). A. B. Charette and J. -F. Marcoux, J. Am. Chem. Soc., 118, 4539 (1996). S. E. Denmark and S. P. O'Connor, J. Org. Chem., 62, 3390 (1997). H. Takahashi, M. Yoshioka, M. Ohno, and S. Kobayashi, Tetrahedron Lett., 33, 2575 (1997).
13. J. H. H-. Chan and B. Richkborn, J. Am. Chem. Soc., 90, 6406 (1968). N. Kawabata, T. Nakagawa, T. Nakao, and S. Yamashita, J. Org. Chem., 42, 3031 (1977). S. E. Denmark, J. P. Edward, and S. R. Wilson, J. Am. Chem. Soc., 114, 2592 (1992). A. B. Charette and C. Brochu, J. Am. Chem. Soc., 117, 11367 (1995). A. B. Charette and J. -F. Marcoux, J. Am. Chem. Soc., 118, 4539 (1996). S. E. Denmark and S. P. O'Connor, J. Org. Chem., 62, 3390 (1997). H. Takahashi, M. Yoshioka, M. Ohno, and S. Kobayashi, Tetrahedron Lett., 33, 2575 (1997).
14. J. H. H-. Chan and B. Richkborn, J. Am. Chem. Soc., 90, 6406 (1968). N. Kawabata, T. Nakagawa, T. Nakao, and S. Yamashita, J. Org. Chem., 42, 3031 (1977). S. E. Denmark, J. P. Edward, and S. R. Wilson, J. Am. Chem. Soc., 114, 2592 (1992). A. B. Charette and C. Brochu, J. Am. Chem. Soc., 117, 11367 (1995). A. B. Charette and J. -F. Marcoux, J. Am. Chem. Soc., 118, 4539 (1996). S. E. Denmark and S. P. O'Connor, J. Org. Chem., 62, 3390 (1997). H. Takahashi, M. Yoshioka, M. Ohno, and S. Kobayashi, Tetrahedron Lett., 33, 2575 (1997).
15. J. H. H-. Chan and B. Richkborn, J. Am. Chem. Soc., 90, 6406 (1968). N. Kawabata, T. Nakagawa, T. Nakao, and S. Yamashita, J. Org. Chem., 42, 3031 (1977). S. E. Denmark, J. P. Edward, and S. R. Wilson, J. Am. Chem. Soc., 114, 2592 (1992). A. B. Charette and C. Brochu, J. Am. Chem. Soc., 117, 11367 (1995). A. B. Charette and J. -F. Marcoux, J. Am. Chem. Soc., 118, 4539 (1996). S. E. Denmark and S. P. O'Connor, J. Org. Chem., 62, 3390 (1997). H. Takahashi, M. Yoshioka, M. Ohno, and S. Kobayashi, Tetrahedron Lett., 33, 2575 (1997).
16. J. H. H-. Chan and B. Richkborn, J. Am. Chem. Soc., 90, 6406 (1968). N. Kawabata, T. Nakagawa, T. Nakao, and S. Yamashita, J. Org. Chem., 42, 3031 (1977). S. E. Denmark, J. P. Edward, and S. R. Wilson, J. Am. Chem. Soc., 114, 2592 (1992). A. B. Charette and C. Brochu, J. Am. Chem. Soc., 117, 11367 (1995). A. B. Charette and J. -F. Marcoux, J. Am. Chem. Soc., 118, 4539 (1996). S. E. Denmark and S. P. O'Connor, J. Org. Chem., 62, 3390 (1997). H. Takahashi, M. Yoshioka, M. Ohno, and S. Kobayashi, Tetrahedron Lett., 33, 2575 (1997).
17. J. H. H-. Chan and B. Richkborn, J. Am. Chem. Soc., 90, 6406 (1968). N. Kawabata, T. Nakagawa, T. Nakao, and S. Yamashita, J. Org. Chem., 42, 3031 (1977). S. E. Denmark, J. P. Edward, and S. R. Wilson, J. Am. Chem. Soc., 114, 2592 (1992). A. B. Charette and C. Brochu, J. Am. Chem. Soc., 117, 11367 (1995). A. B. Charette and J. -F. Marcoux, J. Am. Chem. Soc., 118, 4539 (1996). S. E. Denmark and S. P. O'Connor, J. Org. Chem., 62, 3390 (1997). H. Takahashi, M. Yoshioka, M. Ohno, and S. Kobayashi, Tetrahedron Lett., 33, 2575 (1997).