Use of N,N-Coordinating Ligands in Catalytic Asymmetric C--C Bond Formations: Example of Cyclopropanation, Diels--Alder Reaction, Nucleophilic Allylic Substitution

Schulz, Emmanuelle

doi:10.1007/b136349

Chiral Diazaligands for Asymmetric Synthesis

DOI: 10.1007/b136349

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Use of N,N-Coordinating Ligands in Catalytic Asymmetric C--C Bond Formations: Example of Cyclopropanation, Diels--Alder Reaction, Nucleophilic Allylic Substitution

Emmanuelle Schulz

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Cited by 7 publications

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Chiral Bis(oxazoline) Ruthenium Complexes with Bipyridyl‐Type N‐Heteroaromatics: Comparative Stereochemical and Photochemical Characterization of their Λ‐ and Δ‐Diastereomeric Geminate Isomers

Onishi

Tashiro

Arikawa

et al. 2011

Chemistry An Asian Journal

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Diastereomeric geminate pairs of chiral bis(2-oxazoline) ruthenium complexes with bipyridyl-type N-heteroaromatics, Λ- and Δ-[Ru(L-L)(2)(iPr-biox)](2+) (iPr-biox=(4S,4'S)-4,4'-diisopropyl-2,2'-bis(2-oxazoline); L-L=2,2'-bipyridyl (bpy) for 1Λ and 1Δ, 4,4'-dimethyl-2,2'-bipyridyl (dmbpy) for 2Λ and 2Δ, and 1,10-phenanthroline (phen) for 3Λ and 3Δ), were separated as BF(4) and PF(6) salts and were subjected to the comparative studies of their stereochemical and photochemical characterization. DFT calculations of 1Λ and 1Δ electronic configurations for the lowest triplet excited state revealed that their MO-149 (HOMO) and MO-150 (lower SOMO) characters are interchanged between them and that the phosphorescence-emissive states are an admixture of a Ru-to-biox charge-transfer state and an intraligand excited state within the iPr-biox. Furthermore, photoluminescence properties of the two Λ,Δ-diastereomeric series are discussed with reference to [Ru(bpy)(3)](2+).

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Chiral Bis(oxazoline) Ruthenium Complexes with Bipyridyl‐Type N‐Heteroaromatics: Comparative Stereochemical and Photochemical Characterization of their Λ‐ and Δ‐Diastereomeric Geminate Isomers

Onishi

Tashiro

Arikawa

et al. 2011

Chemistry An Asian Journal

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Synthesis and Sensory Studies of Umami‐Active Scaffolds

Backes

Paetz

Vössing

et al. 2014

Chemistry & Biodiversity

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The class of 2-isopropyl-5-methylbicyclo[4.1.0]heptane-7-carboxamides, 1-4, has been identified as potent umami-tasting molecules. A scalable synthesis of this challenging scaffold and new sensory insights will be presented. Interestingly, the umami characteristics differ remarkably, depending on constitutional and stereochemical features of the parent scaffold. During our studies, we could identify the carboxamide moiety as a crucial factor to influence the umami intensity of these scaffolds. In addition, the configuration of the cyclopropyl moiety exerts some influence, whereas the absolute configuration of the menthyl scaffold, at least the tested D- and L-configuration, is less important.

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