A new route to keto and alkyl derivatives of (R)-carvone via diastereoselective conjugate addition of nitronate ions

The reactivity and diastereoselectivity of conjugate addition of different nitronates ions to (R)-carvone was systematically studied. The Michael adducts 2a-e were obtained in good yield and 3,2-cis-3,5-trans selectivity. The nitroadducts 2b, c were transformed via Nef reaction into (R)-carvone keto...

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Published inJournal of the Brazilian Chemical Society Vol. 17; no. 7; pp. 1229 - 1232
Main Authors Costa, Jeronimo S., Freire, Bruno S., Moura, Andre L. S., Pereira, Vera L. Patrocinio
Format Journal Article
LanguageEnglish
Published SAO PAULO Soc Brasileira Quimica 01.12.2006
Sociedade Brasileira de Química
Subjects
Chemistry
CHEMISTRY, MULTIDISCIPLINARY
Physical Sciences
Science & Technology
Michael addition
DRIMANE SESQUITERPENOIDS
nitroalkyl anions
S-(+)-CARVONE
tetrabutylammonium fluoride
ACETONIDE
Nef reaction
CARVONE
NITROMETHANE
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Summary:The reactivity and diastereoselectivity of conjugate addition of different nitronates ions to (R)-carvone was systematically studied. The Michael adducts 2a-e were obtained in good yield and 3,2-cis-3,5-trans selectivity. The nitroadducts 2b, c were transformed via Nef reaction into (R)-carvone ketone derivatives 9,10 and nitroadducts 2b, d led to (R)-carvone alkylated derivatives 11,12, via a denitration reaction.
ISSN:0103-5053
1678-4790
1678-4790
0103-5053
DOI:10.1590/S0103-50532006000700006