Neighboring group participation of the indole nucleus: An unusual DAST-mediated rearrangerment reaction

Journal of Organic Chemistry

Volumn 65, Issue 16, 2000, Pages 4984-4993

  Hallett, David J ^a   Gerhard, Ute ^a   Goodacre, Simon C ^a   Hitzel, Laure ^a   Sparey, Timothy J ^a   Thomas, Steven ^a   Rowley, Michael ^a   Ball, Richard G ^b  

^a NEUROSCIENCE RESEARCH CENTRE   (United Kingdom)

^b MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ESTER; FLUORIDE; INDOLE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0034637620     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0004759     Document Type: Article

References (18)

1. (a) Closson, W. D.; Roman, S. A.; Kwiatkowski, G. T.; Corwin D. A. Tetrahedron Lett. 1966, 2271.
2. (b) Julia M.; Igolen H.; Lenzi, J. Bull. Soc. Chim. Fr. 1966, 2291.
3. Julia, M.; Sliwa, H.; Caubère, P. Bull. Soc. Chim. Fr.. 1966, 3359.
4. Johansen, J. E.; Christie, B. D.; Rapoport, H. J. Org. Chem. 1981, 46, 4914.
5. Jackson, A. H.; Smith, A. E. Tetrahedron 1968, 24, 403.
6. (a) Ciamician, G.; Plancher, G. Chem. Ber. 1896, 29, 2475.
7. (b) Jackson, A. H.; Smith, P. Tetrahedron 1968, 24, 2227.
8. Direct attack at C-2 can and does occur: (a) Casnati, G.; Dossena, A.; Pochini, A. Tetrahedron Lett. 1972, 5277.
9. (b) Iyer, R.; Jackson, A. H.; Shannon, P. V. R.; Naidoo, B. J. Chem. Soc., Chem. Commun. 1972, 461.
10. Hudlicky, M. Org. React. 1988, 35, 513.
11. Freter, K.; Fuchs, V. J. Heterocycl. Chem. 1982, 19, 377.
12. Pelter, A.; Smith, K.; Brown, H. C. Borane Reagents; Academic Press: London 1988.
13. Van Niel, M. B.; Collins, I.; Beer, M. S.; Broughton, H. B.; Cheng, S. K. F.; Goodacre, S. C.; Heald, A.; Locker, K. L.; MacLeod, A. M.; Morrison, D.; Moyes, C. R.; O'Connor, D.; Pike, A.; Rowley, M.; Russell, M. G. N.; Sohal, B.; Stanton, J. A.; Thomas, S.; Verrier, H.; Watt, A. P.; Castro, J. L. J. Med. Chem. 1999, 42, 2087.
14. Kursanov, D. N.; Parnes, Z. N.; Loim, N. M. Synthesis 1974, 633.
15. Brown, H. C.; Singaram, B. J. Am. Chem. Soc. 1984, 106, 1797.
16. Brown, H. C.; Desai, M. C.; Jadhav, P. K. J. Org. Chem. 1982, 47, 5065.
17. N1 type process.
18. Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923.