A general strategy to spiro[4.n]alk-2-ene-1,6-diones and spiro[5.n]alk- 2-ene-1,7-diones via intramolecular acylation of α-sulfinyl carbanions

Tetrahedron Letters

Volumn 41, Issue 3, 2000, Pages 377-380

  Pohmakotr, Manat ^a   Bunlaksananusorn, Tanasri ^a   Tuchinda, Patoomratana ^a  

^a MAHIDOL UNIVERSITY   (Thailand)

Author keywords

Acylation; Annulation; Carbanions; Spiro compounds; Sulfoxides

Indexed keywords

ALKENE DERIVATIVE; SPIRO COMPOUND; SULFOXIDE;

ACYLATION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; METHODOLOGY; MOLECULAR DYNAMICS;

EID: 0034650831     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01897-3     Document Type: Article

References (16)

1. Taken from an M.Sc. Thesis by T.B., Mahidol University, 1999.
2. For reviews, see: (a) Krapcho, A. P. Synthesis 1974, 383-419. (b) Krapcho, A. P. Synthesis 1978, 77-128. © Sannigrahi, M. Tetrahedron 1999, 55, 9007-9071.
3. For reviews, see: (a) Krapcho, A. P. Synthesis 1974, 383-419. (b) Krapcho, A. P. Synthesis 1978, 77-128. © Sannigrahi, M. Tetrahedron 1999, 55, 9007-9071.
4. For reviews, see: (a) Krapcho, A. P. Synthesis 1974, 383-419. (b) Krapcho, A. P. Synthesis 1978, 77-128. © Sannigrahi, M. Tetrahedron 1999, 55, 9007-9071.
5. Stereoselective synthesis of spirocarbocyclic diones, see: (a) Chitkul, B.; Pinyopropanich, Y.; Thebtaranonth, C.; Thebtaranonth, Y.; Taylor, W. C. Tetrahedron Lett. 1994, 35, 1099-1102. (b) Hayashi, T.; Kanehira, K.; Hagihara, T.; Kumada, M. J. Org. Chem. 1988, 53, 113-120. © Suemune, H.; Maeda, K.; Kato, K.; Sakai, K. J. Chem. Soc., Perkin Trans. 1 1994, 3441-3447. (d) Kato, K.; Suemune, H.; Sakai, K. Tetrahedron 1994, 50, 3315-3326. (e) Tokunaga, Y.; Yagihashi, M.; Ihara, M.; Fukumoto, K. J. Chem. Soc., Chem. Commun. 1995, 955-956.
6. Stereoselective synthesis of spirocarbocyclic diones, see: (a) Chitkul, B.; Pinyopropanich, Y.; Thebtaranonth, C.; Thebtaranonth, Y.; Taylor, W. C. Tetrahedron Lett. 1994, 35, 1099-1102. (b) Hayashi, T.; Kanehira, K.; Hagihara, T.; Kumada, M. J. Org. Chem. 1988, 53, 113-120. © Suemune, H.; Maeda, K.; Kato, K.; Sakai, K. J. Chem. Soc., Perkin Trans. 1 1994, 3441-3447. (d) Kato, K.; Suemune, H.; Sakai, K. Tetrahedron 1994, 50, 3315-3326. (e) Tokunaga, Y.; Yagihashi, M.; Ihara, M.; Fukumoto, K. J. Chem. Soc., Chem. Commun. 1995, 955-956.
7. Stereoselective synthesis of spirocarbocyclic diones, see: (a) Chitkul, B.; Pinyopropanich, Y.; Thebtaranonth, C.; Thebtaranonth, Y.; Taylor, W. C. Tetrahedron Lett. 1994, 35, 1099-1102. (b) Hayashi, T.; Kanehira, K.; Hagihara, T.; Kumada, M. J. Org. Chem. 1988, 53, 113-120. © Suemune, H.; Maeda, K.; Kato, K.; Sakai, K. J. Chem. Soc., Perkin Trans. 1 1994, 3441-3447. (d) Kato, K.; Suemune, H.; Sakai, K. Tetrahedron 1994, 50, 3315-3326. (e) Tokunaga, Y.; Yagihashi, M.; Ihara, M.; Fukumoto, K. J. Chem. Soc., Chem. Commun. 1995, 955-956.
8. Stereoselective synthesis of spirocarbocyclic diones, see: (a) Chitkul, B.; Pinyopropanich, Y.; Thebtaranonth, C.; Thebtaranonth, Y.; Taylor, W. C. Tetrahedron Lett. 1994, 35, 1099-1102. (b) Hayashi, T.; Kanehira, K.; Hagihara, T.; Kumada, M. J. Org. Chem. 1988, 53, 113-120. © Suemune, H.; Maeda, K.; Kato, K.; Sakai, K. J. Chem. Soc., Perkin Trans. 1 1994, 3441-3447. (d) Kato, K.; Suemune, H.; Sakai, K. Tetrahedron 1994, 50, 3315-3326. (e) Tokunaga, Y.; Yagihashi, M.; Ihara, M.; Fukumoto, K. J. Chem. Soc., Chem. Commun. 1995, 955-956.
9. Stereoselective synthesis of spirocarbocyclic diones, see: (a) Chitkul, B.; Pinyopropanich, Y.; Thebtaranonth, C.; Thebtaranonth, Y.; Taylor, W. C. Tetrahedron Lett. 1994, 35, 1099-1102. (b) Hayashi, T.; Kanehira, K.; Hagihara, T.; Kumada, M. J. Org. Chem. 1988, 53, 113-120. © Suemune, H.; Maeda, K.; Kato, K.; Sakai, K. J. Chem. Soc., Perkin Trans. 1 1994, 3441-3447. (d) Kato, K.; Suemune, H.; Sakai, K. Tetrahedron 1994, 50, 3315-3326. (e) Tokunaga, Y.; Yagihashi, M.; Ihara, M.; Fukumoto, K. J. Chem. Soc., Chem. Commun. 1995, 955-956.
10. (a) Pohmakotr, M.; Phinyocheep, P. Tetrahedron Lett. 1984, 25, 2249-2252.
11. (b) Pohmakotr, M.; Chancharunee, S. Tetrahedron Lett. 1984, 25, 4141-4144.
12. © Pohmakotr, M.; Popuang, S. Tetrahedron Lett. 1988, 29, 4189-4190.
13. (d) Pohmakotr, M.; Popuang, S.; Chancharunee, S. Tetrahedron Lett. 1989, 30, 1715.
14. (a) Iwai, K.; Kosugi, H.; Uda, H. Chem. Lett. 1974, 1237-1238.
15. (b) Monteiro, H. J.; Gemal, A. L. Synthesis 1975, 437-438.
16. © Warren, S. Chem. Ind. 1980, 824-828.