Asymmetric induction in [1+4] cycloadditions of vinyl isocyanates with chiral nucleophilic carbenes

Tetrahedron Letters

Volumn 40, Issue 13, 1999, Pages 2473-2476

  Rigby, James H ^a   Cavezza, Alexandre ^a   Heeg, Mary Jane ^a  

^a WAYNE STATE UNIVERSITY   (United States)

Author keywords

Asymmetric induction; Carbenes; Cycloadditions; Indolinones

Indexed keywords

ISOCYANATE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOMER; ISOMER; ISOMERISM; OPTICAL ROTATION; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

EID: 0033605928     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00280-4     Document Type: Article

References (16)

1. For some recent studies on nucleophilic carbenes, see: (a) Arduengo, III, A. J.; Davidson, F.; Dias, H. V. R.; Goerlich, J. R.; Khasnis, D.; Marshall, W. J.; Prakasha, T. K. J. Am. Chem. Soc. 1997, 119, 12742.
2. (b) Couture, P.; Terlouw, J. K.; Warkentin, J. Ibid. 1996, 118, 4214.
3. (c) Arduengo, III, A. J.; Goerlich, J. R.; Marshall, W. J. Ibid. 1995, 117,
4. Rigby, J. H.; Cavezza, A.; Ahmed, G. J. Am. Chem. Soc. 1996, 118, 12848.
5. Rigby, J. H.; Cavezza, A.; Heeg, M. J. J. Am. Chem. Soc. 1998, 120, 3664.
6. For other synthetic uses of nucleophilic carbenes, see: (a) Couture, P.; Warkentin, J. Can. J. Chem. 1998, 76, 241.
7. (b) Ross, J. P.; Couture, P.; Warkentin, J. Ibid. 1997, 75, 1231.
8. (a) Doyle, M. P. Pure Appl. Chem. 1998, 70, 1123.
9. (b) Doyle, M. P. Tetrahedron 1998, 59, 7919.
10. (c) Fürstner, A.; Langemann, K. J. Am. Chem. Soc. 1997, 119, 9130.
11. Corey, E. J.; Carey, F. A.; Winter, R. A. E. J. Am. Chem. Soc. 1965, 87, 934.
12. 2
13. 13C NMR, IR) and analytical (HRMS and/or combustion analysis) data consistent with the assigned structure.
14. 3 solution, concentrated and purified by column chromatography. Yield: 4.3 g (68%).
15. (a) Rossen, K.; Pye, P. J.; DiMichele, L. M.; Volante, R. P.; Reider, P. J. Tetrahedron Lett. 1998, 39, 6823.
16. (b) Askin, D.; Eng, K. K.; Rossen, K.; Purick, R. M.; Wells, K. M.; Volante, R. P.; Reider, P. J. Ibid. 1994, 35, 673.