First stereoselective synthesis of enantiomerically pure telluronium salts by the reaction of chiral halooxatelluranes with Grignard reagents

Tetrahedron Asymmetry

Volumn 8, Issue 20, 1997, Pages 3357-3361

  Zhang, Jian ^a   Saito, Shinichi ^a   Koizumi, Toru ^a  

^a UNIVERSITY OF TOYAMA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

LIGAND; OXATELLURANE DERIVATIVE; REAGENT; TELLURONIUM SALT; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION KINETICS; CHIRALITY; ENANTIOMER; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; X RAY ANALYSIS;

EID: 0030714614     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00459-X     Document Type: Article

References (30)

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25. (g) The halogen exchange reaction of the chiral halooxachalcogenuranes with AgX or NaX (X=halogen) gave the products with retention of configuration at the chalcogen atom throughout the reaction, see: Takahashi, S.; Zhang, J.; Saito, S.; Koizumi, T. Heterocycles, 1997, 44, in press.
26. To express the stereochemical process of the reaction of chiral halooxachalcogenuranes with carbon anion clearly, we use the term "retention" as "the reaction of the halooxachalcogenurane (a) resulted in the formation of the chalcogenium compound (b)". The formation of c is naturally considered as the "inversion" of configuration at the chalcogen atom. figure presented
27. 5d
28. w=7.9%. Selected bond lengths (Å) and angles (deg) are as follows: Te-C(1), 2.16(1); Te-C(2), 2.13(2); Te-C(3), 2.15(1); Te⋯O, 2.84(1); Te⋯Cl, 3.150(3); C(1)-Te-C(2), 93.5(7); C(1)-Te-C(3), 95.8(6); C(2)-Te-C(3), 80.1(7); Cl⋯Te⋯O, 87.8(3); Cl⋯Te-C(1), 90.9(4); Cl⋯Te-C(2), 110.7(5); Cl⋯Te-C(3), 167.0(5); O⋯Te-C(1), 69.4(6); O⋯Te-C(2), 155.4(6); O⋯Te-C(3), 84.1(5). Further details of the crystal structure investigation are available on request from the Director of the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK, on quoting the full journal citation.
29. 25ClOTe: C, 45.15; H, 6.77. Found: C, 45.50; H, 6.73.
30. We confirmed that the absolute configuration of the compounds is not affected by work-up. Koizumi, T. et al., unpublished results.