Enantioselective synthesis of 2-benzothiazolyl oxiranes

Tetrahedron Letters

Volumn 38, Issue 33, 1997, Pages 5843-5846

  Florio, Saverio ^a   Capriati, Vito ^a   Russo, Vincenzo ^a  

^a UNIVERSITY OF BARI   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOTHIAZOLE DERIVATIVE; ETHYLENE OXIDE DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY;

STAPHYLOCOCCUS PHAGE 3A;

EID: 0030807015     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01298-7     Document Type: Article

References (35)

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14. For some recent papers on the use of chiral lithium amides see: a) Uragami, M.; Tomioka, K.; Koga, K. Tetrahedron Asymmetry 1995, 6, 701.
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22. Florio, S.; Troisi, L. Tetrahedron Lett. 1992, 33, 7953.
23. Florio, S.; Troisi, L. J. Org. Chem. 1996, 61, 4148.
24. Florio, S.; Troisi, L.; Capriati, V. J. Org. Chem. 1995, 60, 2279.
25. Vo, D.; Agarwal, K. C.; Knaus, E. E.; Allen, T. M.; Fathi-Afshar, R. Eu. J. Med. Chem. 1988, 23, 39.
26. The ee values were determined by HPLC using a chiral column (Chiracel OD, Daicel Co., Tokyo, Japan) with hexane-isopropanol (90-99.5: 10-0.5, flow rate= 0.35-1 mL/min, monitored at 254 nm).
27. 4Cl after 3h.
28. Kingsbury, C. A.; Durham, D. L.; Hutton, R. J. Org. Chem. 1978, 43, 4696.
29. The methynic ring proton of the E isomer displays dipolar interaction with the vicinal methyl group; the saturation of the latter gives 7.0 enhancement of the ring proton resonance against no detectable enhancement in the case of the other isomer.
30. An example of stereospecific transformation of syn and anti chlorohydrins has recently been reported for 2-halogeno-3-hydroxy esters: Cabon, O.; Buisson, D.; Larcheveque, M.; Azerad, R. Tetrahedron Asymmetry 1995, 6, 2211.
31. The variation in the ee of 3d could be ascribed to the equilibration of the parent halohydrins which may interconvert through a retroaldol-aldol reaction or an enolization reaction considering that 1b has to be seen as an aza-enolate. See: Calò, V.; Lopez, L.; Fiandanese, V.; Naso, F.; Ronzini, L. Tetrahedron Lett. 1978, 4693; Zimmermann, H. E.; Ahramjian, L. J. Am. Chem. Soc. 1960, 82, 5459. Abdel-Magid, A.; Pridgen, L. N.; Eggleston, D. S.; Lantos, I. J. Am. Chem. Soc. 1986, 108, 4595. See also ref. 13.
32. The variation in the ee of 3d could be ascribed to the equilibration of the parent halohydrins which may interconvert through a retroaldol-aldol reaction or an enolization reaction considering that 1b has to be seen as an aza-enolate. See: Calò, V.; Lopez, L.; Fiandanese, V.; Naso, F.; Ronzini, L. Tetrahedron Lett. 1978, 4693; Zimmermann, H. E.; Ahramjian, L. J. Am. Chem. Soc. 1960, 82, 5459. Abdel-Magid, A.; Pridgen, L. N.; Eggleston, D. S.; Lantos, I. J. Am. Chem. Soc. 1986, 108, 4595. See also ref. 13.
33. The variation in the ee of 3d could be ascribed to the equilibration of the parent halohydrins which may interconvert through a retroaldol-aldol reaction or an enolization reaction considering that 1b has to be seen as an aza-enolate. See: Calò, V.; Lopez, L.; Fiandanese, V.; Naso, F.; Ronzini, L. Tetrahedron Lett. 1978, 4693; Zimmermann, H. E.; Ahramjian, L. J. Am. Chem. Soc. 1960, 82, 5459. Abdel-Magid, A.; Pridgen, L. N.; Eggleston, D. S.; Lantos, I. J. Am. Chem. Soc. 1986, 108, 4595. See also ref. 13.
34. This kind of complex, between an organolithium and (-)-sparteine, has been used recently for the successful enantioselective deprotonation of carbamate protected alcohol (Hoppe, D.; Hintze, F.; Tebben, P.; Paelov, M.; Ahrens, H.; Schverdtfeger, J.; Sommerfeld, P.; Haller, J.; Guarnieri, W.; Kolczewski, S.; Hense, T.; Hoppe, I. Pure & Appl. Chem. 1994, 66, 1479) and N-t-Boc-protected pyrrolidine (see Ref. 2e).
35. Diastereomeric chlorohydrins from the reaction of 1b with aldehydes do not interconvert under the reaction conditions. Indeed, the syn chlorohydrin 2e was recovered unchanged after treatment with LDA in the presence of (-)-sparteine.