Efficient conversion of vicinal diols to alkenes by treatment of the corresponding dimesylates with a catalytic, minimally fluorous, recoverable diaryl diselenide and sodium borohydride

Organic Letters

Volumn 2, Issue 25, 2000, Pages 4029-4030

  Crich, David ^a   Neelamkavil, Santhosh ^a   Sartillo Piscil, Fernando ^a,b  

^a UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

^b BENEMÉRITA UNIVERSIDAD AUTÓNOMA DE PUEBLA   (Mexico)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001650216     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0066532     Document Type: Article

References (13)

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3. Crich, D.; Hao, X. Org. Lett. 1999, 1, 269.
4. Crich, D.; Hao, X. Lucas, M. Tetrahedron 1999, 55, 14261.
5. Crich, D.; Barba, G. R. Org. Lett. 2000, 2, 989.
6. Horvath, I. T. Acc. Chem. Res. 1998, 31, 641.
7. de Wolf, E.; van Koten, G.; Deelman, B.-J. Chem. Soc. Rev. 1999, 28, 37.
8. Curran, D. P. Angew. Chem., Int. Ed. Engl. 1998, 37, 1174.
9. Curran, D. P.; Luo, Z. J. Am. Chem. Soc. 1999, 121, 9069.
10. Although we have not attempted any demonstration, we assume that the true nucleophile is the arylseleno(triethoxy)borate: Miyashita, M.; Hoshino, M.; Yoshikoshi, A. Tetrahedron Lett. 1988, 29, 347
11. Habich, D.; Barth, W. Synthesis 1988, 943.
12. Lin, T. S.; Luo, M. Z.; Liu, M. C. Tetrahedron Lett. 1994, 35, 3477.
13. 4 for 2 h. The fluorous diselenide (1) was recovered by evaporation of the FC 72 phase (14.1 mg. 76%) and the olefin (3) by flash chromatography over silica gel using 25% EtOAc-hexane as eluent (31 mg. 74%).