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.
2005
2005
4649
4653
D. Giomi; M. Piacenti; A. Brandi
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Utilizza questo identificatore per citare o creare un link a questa risorsa: https://hdl.handle.net/2158/311113
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