First synthesis and structure of optically pure Te-chiral-alkoxytelluranes

Tetrahedron Asymmetry

Volumn 7, Issue 10, 1996, Pages 2797-2800

  Takahashi, Tamiko ^a   Zhang, Jian ^a   Kurose, Noriyuki ^a   Takahashi, Shigemasa ^a   Koizumi, Toru ^a   Shiro, Motoo ^b  

^a UNIVERSITY OF TOYAMA   (Japan)

^b RIGAKU CORPORATION   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANOTELLURIUM DERIVATIVE;

ARTICLE; CHIRALITY; DRUG PURIFICATION; DRUG STRUCTURE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; STEREOCHEMISTRY; X RAY ANALYSIS;

EID: 0030272168     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00365-5     Document Type: Article

References (24)

1. 1. Recent reviews: (a) Petragnani, N.; Comasseto, J. V. Synthesis, 1986, 1-30; 1991, 793-817, 897-919.
2. 1. Recent reviews: (a) Petragnani, N.; Comasseto, J. V. Synthesis, 1986, 1-30; 1991, 793-817, 897-919.
3. (b) Petragnani, N. Tellurium in Organic Synthesis; Academic Press: London, 1994.
4. 2. For the synthesis of optically active telluronium salts: (a) Lowry, T. M.; Gilbert, F. L. J. Chem. Soc., 1929, 2867-2876.
5. (b) Holliman, F. G.; Mann, F. G. ibid., 1945, 37-44.
6. (c) Shimizu, T.; Urakubo, T.; Kamigata, N. Chem. Lett., 1996, 297-298. For the synthesis of optically active telluronium ylides:
7. (d) Kamigata, N.; Matsuhisa, A.; Taka, H.; Shimizu, T. J. Chem. Soc., Perkin Trans. 1, 1995, 821-827.
8. 3. For designation of "Te-chiral-10-Te-4", see: Perkins, C, W.; Martin, J. C.; Arduengo, A. J., III; Lau, W.; Alegria, A.; Kochi, J. K. J. Am. Chem. Soc., 1980, 102, 7753-7759.
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10. 4. Poth, N. Rev. Tech. Luxemb., 1976, 68, 195-199; Chem. Abstr., 1977, 87, 135965k.
11. 5. Oae, S.; Togo, H. Synthesis, 1981, 371-373.
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14. (b) Ferreira J. T. B.; de Oliveira, A. R. M.; Commasseto, J. V. Synth. Commun., 1989,19, 239-244.
15. 1H NMR, Mass) data were obtained for all new isolable compounds.
16. 1H NMR spectrum of a crude reaction mixture.
17. 10. Designation of absolute configuration at tetracoordinate tellurium (IV) was followed by an extension of the Cahn, Ingold, Prelog (CIP) R-S nomenclature proposed by Martin and Balthazor, see: Martin, J. C.; Balthazor, T. M. J. Am. Chem. Soc., 1977, 99, 152-162.
18. w = 5.2%. Further details of the crystal structure investigation are available on request from the Director of the Cambridge Crystallographic Data Centre, 12 Union Road, GB-Cambridge, CB2 1EZ (UK), on quoting the full journal citation.
19. 12. (a) Berry, F. J.; Edwards, A. J. J. Chem. Soc., Dalton, 1980, 2306-2308.
20. (b) Michalak, R. S.; Wilson, S. R.; Martin, J. C. J. Am. Chem. Soc., 1984, 106, 7529-7539.
21. 3), 1.04-1.97 (m, 7H), 2.60 and 3.55 (AB q, J = 13.2 Hz, 2H, 10-H), 4.06 (dd, J = 3.3, 6.6 Hz, 1H, 3-H), 7.43 (d, 1H, J = 7.1 Hz, vinyl-H), 7.50 (d, 1H, J = 7.1 Hz, vinyl-H). Similar reaction of (E)-1f afforded decomposed products.
22. 14. Takaguchi and Furukawa have reported the synthesis of a racemic spirotellurane which has alkoxy and acyloxy groups as the apical ligands, see: Takaguchi, Y.; Furukawa, N. Chem. Lett., 1996, 365-366.
23. 15. (a) For stabilization of hypervalent species by a five membered ligand, see: Martin, J. C. Science, 1983, 221, 509-514.
24. (b) We have developed this concept of steric protection into the first synthesis of optically pure selenuranes, see: Takahashi, T.; Kurose, N.; Kawanami, S.; Arai, Y.; Koizumi, T.; Shiro, M. J. Org. Chem., 1994, 59, 3262-3264.