Tandem reductive lithiations - Carbanionic cyclizations yielding sulfur stabilized cyclopropyl- and cyclobutylcarbinyllithiums

Tetrahedron

Volumn 55, Issue 11, 1999, Pages 3291-3304

  Chen, Fangping ^a   Mudryk, Boguslaw ^a   Cohen, Theodore ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; CYCLOBUTANE DERIVATIVE; CYCLOPROPANE DERIVATIVE; LITHIUM DERIVATIVE; SULFUR;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; METHODOLOGY; PRIORITY JOURNAL; REDUCTION; SYNTHESIS;

EID: 0033104461     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)01141-7     Document Type: Article

References (30)

1. Taken in part from the M.S. thesis of F. Chen, University of Pittsburgh, 1995.
2. Cohen, T.; Bhupathy, M. Acc. Chem. Res. 1989, 22, 152-161. For the discovery of this method of organolithium production, see: Screttas, C. G.; Micha-Screttas, M. J. Org. Chem. 1978, 43, 1064-1071; 1979, 44, 713-719. Cohen, T.; Daniewski, W. M.; Weisenfeld, R. B. Tetrahedron Lett. 1978, 4665- 4668.
3. Cohen, T.; Bhupathy, M. Acc. Chem. Res. 1989, 22, 152-161. For the discovery of this method of organolithium production, see: Screttas, C. G.; Micha-Screttas, M. J. Org. Chem. 1978, 43, 1064-1071; 1979, 44, 713-719. Cohen, T.; Daniewski, W. M.; Weisenfeld, R. B. Tetrahedron Lett. 1978, 4665- 4668.
4. Cohen, T.; Bhupathy, M. Acc. Chem. Res. 1989, 22, 152-161. For the discovery of this method of organolithium production, see: Screttas, C. G.; Micha-Screttas, M. J. Org. Chem. 1978, 43, 1064-1071; 1979, 44, 713-719. Cohen, T.; Daniewski, W. M.; Weisenfeld, R. B. Tetrahedron Lett. 1978, 4665- 4668.
5. Cohen, T.; Bhupathy, M. Acc. Chem. Res. 1989, 22, 152-161. For the discovery of this method of organolithium production, see: Screttas, C. G.; Micha-Screttas, M. J. Org. Chem. 1978, 43, 1064-1071; 1979, 44, 713-719. Cohen, T.; Daniewski, W. M.; Weisenfeld, R. B. Tetrahedron Lett. 1978, 4665- 4668.
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12. After completion the work reported here, we became aware of two reports of carbanionic cyclizations to form sulfur-stabilized cyclopentylcarbinyllithiums; the ring strain in the latter system is of course not comparable to that in the systems that we report here. In the first publication, only primary organolithiums were studied: Kim, S.; Kim, B. S.; Jon, S. Y. Bull. Korean Chem. Soc. 1994, 15, 701. In the second, a tertiary benzylic alkyllithium was used: Krief, A.; Kenda, B.; Remacle, B. Tetrahedron 1996, 52, 7435-7463.
13. After completion the work reported here, we became aware of two reports of carbanionic cyclizations to form sulfur-stabilized cyclopentylcarbinyllithiums; the ring strain in the latter system is of course not comparable to that in the systems that we report here. In the first publication, only primary organolithiums were studied: Kim, S.; Kim, B. S.; Jon, S. Y. Bull. Korean Chem. Soc. 1994, 15, 701. In the second, a tertiary benzylic alkyllithium was used: Krief, A.; Kenda, B.; Remacle, B. Tetrahedron 1996, 52, 7435-7463.
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