Diastereoselective [2+2] photocycloaddition of chiral cyclohexenonecarboxylates to ethylene
Ken Tsutsumi
Graduate School of Materials Science, Nara Institute of Science and Technology (NAIST), Takayama, Ikoma, Nara, Japan
Search for more papers by this authorKatsunori Endou
Graduate School of Materials Science, Nara Institute of Science and Technology (NAIST), Takayama, Ikoma, Nara, Japan
Search for more papers by this authorAkinori Furutani
Graduate School of Materials Science, Nara Institute of Science and Technology (NAIST), Takayama, Ikoma, Nara, Japan
Search for more papers by this authorTomomi Ikki
Graduate School of Materials Science, Nara Institute of Science and Technology (NAIST), Takayama, Ikoma, Nara, Japan
Search for more papers by this authorHiroaki Nakano
Graduate School of Materials Science, Nara Institute of Science and Technology (NAIST), Takayama, Ikoma, Nara, Japan
Search for more papers by this authorTakuya Shintani
Graduate School of Materials Science, Nara Institute of Science and Technology (NAIST), Takayama, Ikoma, Nara, Japan
Search for more papers by this authorTsumoru Morimoto
Graduate School of Materials Science, Nara Institute of Science and Technology (NAIST), Takayama, Ikoma, Nara, Japan
Search for more papers by this authorCorresponding Author
Kiyomi Kakiuchi
Graduate School of Materials Science, Nara Institute of Science and Technology (NAIST), Takayama, Ikoma, Nara, Japan
Graduate School of Materials Science, Nara Institute of Science and Technology (NAIST), Takayama, Ikoma, Nara 630-0101, JapanSearch for more papers by this authorKen Tsutsumi
Graduate School of Materials Science, Nara Institute of Science and Technology (NAIST), Takayama, Ikoma, Nara, Japan
Search for more papers by this authorKatsunori Endou
Graduate School of Materials Science, Nara Institute of Science and Technology (NAIST), Takayama, Ikoma, Nara, Japan
Search for more papers by this authorAkinori Furutani
Graduate School of Materials Science, Nara Institute of Science and Technology (NAIST), Takayama, Ikoma, Nara, Japan
Search for more papers by this authorTomomi Ikki
Graduate School of Materials Science, Nara Institute of Science and Technology (NAIST), Takayama, Ikoma, Nara, Japan
Search for more papers by this authorHiroaki Nakano
Graduate School of Materials Science, Nara Institute of Science and Technology (NAIST), Takayama, Ikoma, Nara, Japan
Search for more papers by this authorTakuya Shintani
Graduate School of Materials Science, Nara Institute of Science and Technology (NAIST), Takayama, Ikoma, Nara, Japan
Search for more papers by this authorTsumoru Morimoto
Graduate School of Materials Science, Nara Institute of Science and Technology (NAIST), Takayama, Ikoma, Nara, Japan
Search for more papers by this authorCorresponding Author
Kiyomi Kakiuchi
Graduate School of Materials Science, Nara Institute of Science and Technology (NAIST), Takayama, Ikoma, Nara, Japan
Graduate School of Materials Science, Nara Institute of Science and Technology (NAIST), Takayama, Ikoma, Nara 630-0101, JapanSearch for more papers by this authorAbstract
The diastereoselective [2+2] photocycloaddition of cyclohexenonecarboxylates containing various chiral auxiliaries to ethylene is described. The effect of the auxiliary, reaction temperature, and solvent on diastereoselectivity was examined. The (−)-8-(p-methoxyphenyl)menthyl group was found to be the most effective chiral auxiliary. The photoreaction of (−)-8-(p-methoxyphenyl)menthyl cyclohexenonecarboxylate in methylcyclohexane at −78°C gave the corresponding bicyclo[4.2.0]octanone derivative in 81% diastereomeric excess (d.e.). The extent of diastereoselectivity was found to be closely related to the most stable π-stack conformation of the starting cyclohexenones. Chirality 15:504–509, 2003. © 2003 Wiley-Liss, Inc.
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