Divergent behavior of cobalt-complexed enyne having a leaving group

Tetrahedron Letters

Volumn 40, Issue 24, 1999, Pages 4563-4566

  Kitamura, Mitsuru ^a   Ohmori, Ken ^a   Suzuki, Keisuke ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

COBALT COMPLEX; CYCLOBUTANE;

ARTICLE; CHEMICAL REACTION; CONFORMATIONAL TRANSITION; CYCLIZATION; STRUCTURE ANALYSIS;

EID: 0033546234     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00791-1     Document Type: Article

References (14)

1. 1. Nagasawa, T.; Suzuki, K. Synlett 1993, 29.
2. 2. Olah, G. A.; Prakash Reddy, V.; Surya Prakash, G. K. Chem. Rev 1992, 92, 69.
3. 3. Nicholas, K. M. Acc. Chem. Res. 1987, 20, 207.
4. 4. For the extension of this idea, see Nagasawa, T.; Taya, K.; Kitamura, M.; Suzuki, K. J. Am. Chem. Soc. 1996, 118, 8949; Taya, K.; Nagasawa, T.; Suzuki, K. Synlett 1997, 304.
5. 4. For the extension of this idea, see Nagasawa, T.; Taya, K.; Kitamura, M.; Suzuki, K. J. Am. Chem. Soc. 1996, 118, 8949; Taya, K.; Nagasawa, T.; Suzuki, K. Synlett 1997, 304.
6. 5. Nagasawa, T.; Kitamura, M.; Suzuki, K. Synlett 1995, 1183.
7. 3A1, see Maruoka, K.; Miyazaki, T.; Ando, M.; Matsumura, Y.; Sakane, S.; Hattori, K.; Yamamoto, H. J. Am. Chem. Soc. 1983, 105, 2831; Suzuki, K.; Tomooka, K.; Katayama, E.; Matsumoto, T.; Tsuchihashi, G. J. Am. Chem. Soc. 1986, 108, 5221.
8. 3A1, see Maruoka, K.; Miyazaki, T.; Ando, M.; Matsumura, Y.; Sakane, S.; Hattori, K.; Yamamoto, H. J. Am. Chem. Soc. 1983, 105, 2831; Suzuki, K.; Tomooka, K.; Katayama, E.; Matsumoto, T.; Tsuchihashi, G. J. Am. Chem. Soc. 1986, 108, 5221.
9. 13C NMR, IR, and HRMS and/or combustion analysis. (Matrix presented)
10. 8. Oxidative decomplexation of 3-5 (CAN, MeOH, room temperature) gave the corresponding alkynes 19-21 in high yields.
11. 4). The stereochemistry of 5 was similarly assigned. (Matrix presented)
12. 13C NMR, DEPT, H-H COSY, HMQC and HMBC.
13. 11. The diastereomers of 2c, separable by silica-gel preparative TLC, showed essentially the same reactivities in this reaction. Unfortunately, their relative configurations could not be assigned. (Matrix presented)
14. 12. Formation of 17 could be rationalized by the isomerization of 18 caused by the protic acid produced by the formation of 16. The (E)-geometry was assigned by the NOE experiment.