Regiospecific Ene Reaction of Benzenesulfinyl Chloride with Linear Isoprenoids

A. M. Moiseenkov; V. A. Dragan; V. A. Koptenkova; V. V. Veselovsky

doi:10.1055/s-1987-28082

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Synthesis 1987; 1987(9): 814-815
DOI: 10.1055/s-1987-28082

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Regiospecific Ene Reaction of Benzenesulfinyl Chloride with Linear Isoprenoids

A. M. Moiseenkov^* , V. A. Dragan, V. A. Koptenkova, V. V. Veselovsky

^*N. D. Zelinsky Institute of Organic Chemistry, Academy of Sciences, Moscow, U. S. S. R.

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Publication Date:
12 September 2002 (online)

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The Lewis acid (e.g., ZnCl₂) catalyzed ene reaction of benzenesulfinyl chloride with myrcene, geranyl and neryl acetates, as well as ethyl (E,E)-farnesoate proceeds smoothly and chemoselectively by exclusive attack at the terminal trisubstituted C=C bond to give allylic sulfoxides.

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