Stereospecific conversion of iodohydrin derivatives into alkenes by means of an allylsilane-titanium tetrachloride system and its application to steseoretentive deoxygenation of epoxides

Tetrahedron Letters

Volumn 38, Issue 29, 1997, Pages 5161-5164

  Yachi, Kentaro ^a   Maeda, Katsuya ^a   Shinokubo, Hiroshi ^a   Oshima, Koichiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; EPOXIDE; TITANIUM DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CIS TRANS ISOMERISM; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0030837499     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01117-9     Document Type: Article

References (16)

1. Maeda, K.; Shinokubo, H.; Oshima, K. J. Org. Chem. 1996, 61, 6770-6771.
2. The starting acetoxyiodoalkanes were prepared from the corresponding iodohydrins. Very recently samarium-mediated stereoselective synthesis of iodohydrins from 1,1-diiodoalkanes and aldehydes has been reported. Matsubara, S.; Yoshioka, M.; Utimoto, K. Angew. Chem. Int. Ed. Engl. 1997, 36, 617-618.
3. 11) resulted in formation of complex mixture.
4. Treatment of 3 with titanium tetrachloride-allyltrimethylsilane provided tri-substituted alkene in 78% yield. formula presented 3 : erythrolthreo = 7/93 E/Z = 22/78
5. 4 would provide alkenes via anti-periplanar elimination.
6. Kochi, J. K.; Singleton, D. M.; Andrews, L. J. Tetrahedron, 1968, 24, 3503-3515.
7. Sharpless, K. B.; Umbreit, M. A.; Nieh, M. T.; Flood, T. C. J. Am. Chem. Soc. 1972, 94, 6538-6540.
8. McMurry, J. E.; Silverstri, M. G.; Fleming, M. P.; Hoz, T.; Grayston, M. W. J. Org. Chem. 1978, 43, 3249-3255.
9. Sato, M.; Oshima, K. Chem. Lett. 1982, 157-160.
10. Fujisawa, T.; Sugimoto, K.; Ohta, H. Chem. Lett. 1974, 883-886.
11. Other retentive deoxygenation of epoxide has been reported. Sonnet, P. E. J. Org. Chem. 1978, 43, 1841-1842; idem. Synthesis 1980, 828-830; Caputo, R.; Mangoni, L.; Neri, O.; Palumbo. G. Tetrahedron Lett. 1981, 22, 3551-3552; Matsubara, S.; Nonaka, T.; Okuda, Y.; Kanemoto, S.; Oshima, K.; Nozaki, H. Bull. Chem. Soc. Jpn. 1985, 58, 1480-1483.
12. Other retentive deoxygenation of epoxide has been reported. Sonnet, P. E. J. Org. Chem. 1978, 43, 1841-1842; idem. Synthesis 1980, 828-830; Caputo, R.; Mangoni, L.; Neri, O.; Palumbo. G. Tetrahedron Lett. 1981, 22, 3551-3552; Matsubara, S.; Nonaka, T.; Okuda, Y.; Kanemoto, S.; Oshima, K.; Nozaki, H. Bull. Chem. Soc. Jpn. 1985, 58, 1480-1483.
13. Other retentive deoxygenation of epoxide has been reported. Sonnet, P. E. J. Org. Chem. 1978, 43, 1841-1842; idem. Synthesis 1980, 828-830; Caputo, R.; Mangoni, L.; Neri, O.; Palumbo. G. Tetrahedron Lett. 1981, 22, 3551-3552; Matsubara, S.; Nonaka, T.; Okuda, Y.; Kanemoto, S.; Oshima, K.; Nozaki, H. Bull. Chem. Soc. Jpn. 1985, 58, 1480-1483.
14. Other retentive deoxygenation of epoxide has been reported. Sonnet, P. E. J. Org. Chem. 1978, 43, 1841-1842; idem. Synthesis 1980, 828-830; Caputo, R.; Mangoni, L.; Neri, O.; Palumbo. G. Tetrahedron Lett. 1981, 22, 3551-3552; Matsubara, S.; Nonaka, T.; Okuda, Y.; Kanemoto, S.; Oshima, K.; Nozaki, H. Bull. Chem. Soc. Jpn. 1985, 58, 1480-1483.
15. 2SiLi proceeded stereospecifically to give an olefin of geometry opposite to that of the starting epoxide. (1) Dervan, P. B.; Shippey, M. A. J. Am. Chem. Soc. 1976, 98, 1265-1267.
16. Reetz, M. T.; Plachky, M. Synthesis, 1976, 199-200.