title: Diastereoselective syntheses of substituted cis-hydrindanones featuring sequential inter- and intramolecular Michael reactions.
abstract: The hydrindane (bicyclo[4.3.0]nonane) structural motif (1) and relatedcis-1-hydrindanone skeleton (2) are common substructures in many natural products. Herein, we describe efficient access to substitutedcis-1-hydrindanones enabled by a sequence of Michael reactions. A copper-catalyzed intermolecular Michael addition of a cyclic silyl ketene acetal to aβ-substituted-α-alkoxycarbonyl-cyclopentenone enables construction of a quaternary center and is followed, after incorporation of an additional Michael acceptor, by a second, intramolecular addition of a nucleophilicβ-ketoester. This strategy affords stereoselective access to substituted bicycliccis-hydrindanone ring systems containing up to three contiguous stereocenters.
authors.affiliation: Department of Chemistry, Princeton University, Frick Chemical Laboratory, Princeton, NJ 08544, USA.
authors.forename: Junjia
authors.initials: J
authors.lastname: Liu
authors.affiliation: Department of Chemistry, Princeton University, Frick Chemical Laboratory, Princeton, NJ 08544, USA.
authors.forename: Maurice A
authors.initials: MA
authors.lastname: Marsini
authors.affiliation: Department of Chemistry, Princeton University, Frick Chemical Laboratory, Princeton, NJ 08544, USA.
authors.forename: T Aaron
authors.initials: TA
authors.lastname: Bedell
authors.affiliation: Department of Chemistry, Princeton University, Frick Chemical Laboratory, Princeton, NJ 08544, USA.
authors.forename: Paul J
authors.initials: PJ
authors.lastname: Reider
authors.affiliation: Department of Chemistry, Princeton University, Frick Chemical Laboratory, Princeton, NJ 08544, USA.
authors.forename: Erik J
authors.initials: EJ
authors.lastname: Sorensen
keywords: 1,4-addition; Michael reaction; conjugate addition; hydrindanone; linchpin; olefin cross metathesis