title: Guide to Enantioselective Dirhodium(II)-Catalyzed Cyclopropanation with Aryldiazoacetates.
abstract: Catalytic enantioselective methods for the generation of cyclopropanes has been of longstanding pharmaceutical interest. Chiral dirhodium(II) catalysts prove to be an effective means for the generation of diverse cyclopropane libraries. Rh2(R-DOSP)4is generaally the most effective catalyst for asymmetric intermolecular cyclopropanation of methyl aryldiazoacetates with styrene. Rh2(S-PTAD)4provides high levels of enantioinduction withortho-substituted aryldiazoacetates. The less-established Rh2(R-BNP)4plays a complementary role to Rh2(R-DOSP)4and Rh2(S-PTAD)4in catalyzing highly enantioselective cyclopropanation of 3- methoxy-substituted aryldiazoacetates. Substitution on the styrene has only moderate influence on the asymmetric induction of the cyclopropanation.
authors.affiliation: Department of Chemistry, Emory University, (404)727-6839, 1515 Dickey Drive, Atlanta, Georgia 30322, USA.
authors.forename: Kathryn M
authors.initials: KM
authors.lastname: Chepiga
authors.forename: Changming
authors.initials: C
authors.lastname: Qin
authors.forename: Joshua S
authors.initials: JS
authors.lastname: Alford
authors.forename: Spandan
authors.initials: S
authors.lastname: Chennamadhavuni
authors.forename: Timothy M
authors.initials: TM
authors.lastname: Gregg
authors.forename: Jeremy P
authors.initials: JP
authors.lastname: Olson
authors.forename: Huw M L
authors.initials: HM
authors.lastname: Davies
keywords: Asymmetric cyclopropanation; Cyclopropanes; Dirhodium catalysis; Donor/acceptor carbenoids; Phenyldiazoacetate