35926-04-6Relevant articles and documents
Overman,L.E.,Campbell,C.B.
, p. 3338 - 3340 (1976)
Ascaroside Signaling in the Bacterivorous Nematode Caenorhabditis remanei Encodes the Growth Phase of Its Bacterial Food Source
Dolke, Franziska,Dong, Chuanfu,Bandi, Siva,Paetz, Christian,Glauser, Gaétan,Von Reu?, Stephan H.
supporting information, p. 5832 - 5837 (2019/08/26)
A novel class of species-specific modular ascarosides that integrate additional fatty acid building blocks was characterized in the nematode Caenorhabditis remanei using a combination of HPLC-ESI-(-)-MS/MS precursor ion scanning, microreactions, HR-MS/MS, MSn, and NMR techniques. The structure of the dominating component carrying a cyclopropyl fatty acid moiety was established by total synthesis. Biogenesis of this female-produced male attractant depends on cyclopropyl fatty acid synthase (cfa), which is expressed in bacteria upon entering their stationary phase.
Regioselective Asymmetric Allylic Alkylation Reaction of α -Cyanoacetates Catalyzed by a Heterobimetallic Platina-/Palladacycle
Weiss, Marcel,Holz, Julia,Peters, Ren
, p. 210 - 227 (2016/01/20)
Allylic substitution reactions provide a valuable tool for the functionalization of CH acidic pronucleophiles. Often, control over the stereocenter generated at the nucleophilic reactant is still a challenge. The majority of studies that address this issue employ metal complexes with a low metal oxidation state (e.g. Pd0) to form allyl complexes through oxidative addition. In this article we describe the use of heterobimetallic PtII/PdII complexes, which probably activate the olefinic substrates through an SN2′ pathway. The reaction of α-cyanoacetates delivers linear allylation products with exclusive regioselectivity and high E/Z-selectivity for the new C=C double bond. Although the enantioselectivities attained are moderate, they are significantly higher than with related mono-PdII or -PtII catalysts or the corresponding bis-PdII complex, which indicates cooperation of the different metals. Control experiments suggest simultaneous activation of both reaction partners.