A novel reactivity of SeO2 with 1,3-dienes: Formation of syn 1,2-and 1,4-diols via a facile C-Se bond oxidation

Organic Letters

Volumn 3, Issue 20, 2001, Pages 3161-3163

  Nguyen, True M ^a   Lee, Daesung ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ALKENE; ORGANOSELENIUM DERIVATIVE; SELENIUM DERIVATIVE; SELENIUM OXIDE;

ARTICLE; CHEMISTRY; OXIDATION REDUCTION REACTION; SYNTHESIS;

ALCOHOLS; ALKENES; ORGANOSELENIUM COMPOUNDS; OXIDATION-REDUCTION; SELENIUM COMPOUNDS;

EID: 0035807538     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016462e     Document Type: Article

References (24)

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14. 4 filter solution. The eis isomer was isolated at 60% conversion in 50% yield and was converted to 9 via reduction followed by silyl protection; 10 was similarly prepared (see Supporting Information).
15. 2, and monitored by NMR spectroscopy.
16. McFarlane, H. C. E.; McFarlane, W. In NMR of Newly Accessible Nuclei, Vol. 2; Laszlo, P. Ed.; Academic Press: New York, 1983; pp 275-299 and references therein.
17. 2, resulted in the ring opening of the cyclic selenite.
18. In the conditions for the rearrangement of 13 to 16, 1,4-diketone 32 and the corresponding hydroxyketone 33 were obtained (see Supporting Information).
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20. 2 to trans-dienes 3 resulted in the formations of diols 14, 17, 21, and 25.
21. 2 at 40 °C did not lead to any expected 1,2-diol 25, and instead 1,2-diol 17 was isolated. It is believed that under the reaction conditions 19 rearranged to 5 via a benzylic cation.
22. 4/NMO at 50 °C.
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24. 3 directly produced 1,2-cyclic selenite 24. The 1,4-cyclic selenite 20 was not observed.