Synthesis p. 895 - 897 (1994)
Update date:2022-08-16
Topics:
Shono
Chuankamnerdkarn
Maekawa
Ishifune
Kashimura
When NO-3 is electrochemically oxidized in the presence of a variety of terminal and 1,2-disubstituted olefins 1 in a mixed solvent system (MeCN:H2O:Et2O = 10:2:1), a radical NO.3 is generated from NO-3 and nitrate esters 3 are formed by a new coupling reaction of the olefin with the radical. The products 3 can be further transformed into the corresponding alcohols 4 and alkyl iodides 5. Under the same reaction conditions, 1,1-di- and 1,1,2-trisubstituted olefins 6 do not give nitrate esters but afford oxazoline derivatives 7. (1S,5S)-(-)-β-Pinene (13) is diastereoselectively transformed into (1S,2R,5S)-(-)-myrtanol (14) by this technique.
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