title: A Scalable Protocol for the Regioselective Alkylation of 2-Methylcyclohexane-1,3-dione with Unactivated sp3Electrophiles.
abstract: A method for the C-selective alkylation of 2-methylcyclohexane-1,3-dione with unactivated sp3electrophiles is accomplished via alkylation and subsequent deprotection of the derived ketodimethyl hydrazones. The present method provides a high-yielding entry to dialkyl cycloalkanones that cannot be accessed via direct alkylation of 2-methylcyclohexane-1,3-dione. The title reaction may be useful in the scalable preparation of terpene and steroidal building blocks in the arena of natural product synthesis.
authors.affiliation: Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, NC 27599-3290, USA.
authors.forename: Robert J
authors.initials: RJ
authors.lastname: Sharpe
authors.affiliation: Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, NC 27599-3290, USA.
authors.forename: Maribel
authors.initials: M
authors.lastname: Portillo
authors.affiliation: Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, NC 27599-3290, USA.
authors.forename: Robert A
authors.initials: RA
authors.lastname: Vélez
authors.affiliation: Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, NC 27599-3290, USA.
authors.forename: Jeffrey S
authors.initials: JS
authors.lastname: Johnson
keywords: alkyl halides; alkylation; hydrazones; ketones; regioselectivity; steroids; terpenoids