Conjugate addition of vinyl cuprate and dimethyl malonate to 4,4-dimethylcyclohexa-2,5-dienones has allowed facile access to mono- and bis-adducts in satisfactory yields. While the high diastereoselectivity of such processes to afford transbis- adducts was predictable, an unprecedented regioselectivity was observed with 2,4,4-trimethylcyclohexa-2,5-dienone, with the first addition occurring exclusively at the C-5 carbon atom (distal from the methyl group) and with the second addition of a bulky nucleophile such as dimethyl malonate even prevented.
Regio- and diastereoselective conjugate additions to 4,4-dimethylcyclohexadienones / D. Giomi; M. Piacenti; A. Brandi. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - STAMPA. - 2005:(2005), pp. 4649-4653. [10.1002/ejoc.200500426]
Regio- and diastereoselective conjugate additions to 4,4-dimethylcyclohexadienones
GIOMI, DONATELLA;BRANDI, ALBERTO
2005
Abstract
Conjugate addition of vinyl cuprate and dimethyl malonate to 4,4-dimethylcyclohexa-2,5-dienones has allowed facile access to mono- and bis-adducts in satisfactory yields. While the high diastereoselectivity of such processes to afford transbis- adducts was predictable, an unprecedented regioselectivity was observed with 2,4,4-trimethylcyclohexa-2,5-dienone, with the first addition occurring exclusively at the C-5 carbon atom (distal from the methyl group) and with the second addition of a bulky nucleophile such as dimethyl malonate even prevented.File | Dimensione | Formato | |
---|---|---|---|
EJOC-Conjugate Addn.pdf
Accesso chiuso
Tipologia:
Versione finale referata (Postprint, Accepted manuscript)
Licenza:
Tutti i diritti riservati
Dimensione
117.69 kB
Formato
Adobe PDF
|
117.69 kB | Adobe PDF | Richiedi una copia |
I documenti in FLORE sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.