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Diastereoselective [2+2] photocycloaddition of chiral cyclohexenonecarboxylates to ethylene
Author(s) -
Tsutsumi Ken,
Endou Katsunori,
Furutani Akinori,
Ikki Tomomi,
Nakano Hiroaki,
Shintani Takuya,
Morimoto Tsumoru,
Kakiuchi Kiyomi
Publication year - 2003
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.10236
Subject(s) - chemistry , methylcyclohexane , diastereomer , chirality (physics) , chiral auxiliary , ethylene , derivative (finance) , solvent , bicyclic molecule , stereochemistry , organic chemistry , medicinal chemistry , enantioselective synthesis , chiral symmetry , catalysis , physics , quantum mechanics , financial economics , nambu–jona lasinio model , economics , quark
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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