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J Am Chem Soc ; 124(11): 2402-3, 2002 Mar 20.
Article in English | MEDLINE | ID: mdl-11890765

ABSTRACT

The utilization of enones as latent enolates enables regioselective enolate formation from chemically robust presursors. In this communication, we report a catalytic Michael cycloisomerization of bis(enones) under Morita-Baylis-Hillman conditions. Upon exposure to 10 mol % tributylphosphine, bis(enone) substrates afford both five- and six-membered ring products. Notably, unsymmetrical bis(enones) possessing sufficient steric or electronic bias yield single isomeric products.


Subject(s)
Alkenes/chemistry , Hydrocarbons, Cyclic/chemical synthesis , Ketones/chemistry
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