Tandem Wagner-Meerwein rearrangement-carbocation trapping in the formation of chiral heterocyclic ring systems

Tetrahedron Letters

Volumn 38, Issue 12, 1997, Pages 2159-2162

  Starling, Scott M ^a   Vonwiller, Simone C ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; ANILINE; FUSED HETEROCYCLIC RINGS; HETEROCYCLIC COMPOUND; PHENOL DERIVATIVE; REAGENT;

ARTICLE; CHEMICAL REACTION; DEMETHYLATION; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0031585052     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00271-2     Document Type: Article

References (15)

1. 1. Haynes, R. K.; Starling, S. M.; Vonwiller, S. C. J. Org. Chem. 1995, 60, 4690.
2. 2. Snieckus, V. Chem. Rev. 1990, 90, 879.
3. 3. Fuhrer, W.; Gschwend, H. W. J. Org. Chem. 1979, 44, 1133.
4. 4. cf Ashby, E. C; Laemmle, J. T. Chem. Rev. 1975, 75, 521; Dimitrov, V.; Simova, S.; Kostova, K. Tetrahedron 1996, 52, 1699.
5. 4. cf Ashby, E. C; Laemmle, J. T. Chem. Rev. 1975, 75, 521; Dimitrov, V.; Simova, S.; Kostova, K. Tetrahedron 1996, 52, 1699.
6. 5. Sorensen, T. S. Acc. Chem. Res. 1976, 9, 257.
7. 6. The absence of trapping by ethanol suggests that steric crowding around the cationic centre is substantial.
8. 7. For other examples of tandem Wagner-Meerwein rearrangement-cation trapping reactions that form hetereocycles see: McCapra, F.; Beheshti, I. J. Chem. Soc., Chem. Commun. 1977, 517; Dimitrov, V.; Philipova, I.; Simova, S. Tetrahedron: Asymmetry 1996, 7, 1493
9. 7. For other examples of tandem Wagner-Meerwein rearrangement-cation trapping reactions that form hetereocycles see: McCapra, F.; Beheshti, I. J. Chem. Soc., Chem. Commun. 1977, 517; Dimitrov, V.; Philipova, I.; Simova, S. Tetrahedron: Asymmetry 1996, 7, 1493
10. 8. Wender, P. A.; White, A. W. Tetrahedron Lett. 1981, 1475.
11. 3, partial): 19 δ 0.94 (2×3H, s), 1.20 (3H, s), 2.46 (1H, ddd, J = 12.5, 3.2, 3.2 Hz); 21 δ 0.76 (3H, s), 0.90 (3H, s), 1.28 (3H, s), 2.65 (1H, ddd, J = 13.4, 3.1, 3.1 Hz); 22 δ 1.18 (3H, s), 1.23 (3H, s), 1.36 (3H, s), 2.22 (1H, dd, J = 4.4, 1.6 Hz).
12. 10. Stern, R.; English, J. Jr.; Cassidy, H. G. J. Am. Chem. Soc. 1957, 79, 5797.
13. 11. The dihydrobenzofurans could only be separated partially by reverse phase HPLC.
14. 12. Levine, R.; Sommers, J. R. J. Org. Chem. 1974, 39, 3559.
15. 13. The rearrangements may be induced by the developing positive charge on the benzylic carbon and may not necessarily involve a discrete carbocation.