Perfluorobutanesulfonyl fluoride - 1,8-Diazabicyclo[5.4.0]undec-7-ene as a useful system in diol-epoxide transformation

Tetrahedron Letters

Volumn 37, Issue 42, 1996, Pages 7497-7498

  Klar, Ulrich ^a   Neef, Günter ^a   Vorbrüggen, Helmut ^a  

^a BAYER PHARMA AG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

1,8 DIAZABICYCLO[5.4.0]UNDECANE DERIVATIVE; BICYCLO COMPOUND; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030583489     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01710-8     Document Type: Article

References (16)

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12. 16)).
13. 13) To a solution of triol 3 (134 mg, 423 μmol) in 4 ml of toluene and 190 μl DBU (1.26 mmol) is added via syringe n-perfluorobutanesulfonyl fluoride (83 μl, 460 μmol) at 0°C. Stirring is continued for 60 minutes at 0°C and workup is performed as already described for the preparation of 2. Chromatography on silica gel with n-hexane/ethyl acetate yields 93 mg epoxide 4 (312 μmol, 73.7%). The configuration at C-9 was confirmed by NMR techniques (NOESY, COSY).
14. 14) N. Iranpoor, I.M. Baltork Synth. Commun. 1990, 20, 2789-1797.
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16. 16) G. Neef, G. Ast, H. Vierhufe Ger. Offen. DE 3 630 030 (Schering AG); Chem. Abstr. 1988, 109, 93425z.