74192-91-9Relevant academic research and scientific papers
Cobalt-Catalyzed Desymmetric Isomerization of Exocyclic Olefins
Lan, Yu,Liu, Qiang,Liu, Shihan,Liu, Xufang,Rong, Xianle
supporting information, p. 20633 - 20639 (2021/12/17)
Chiral cyclic olefins, 1-methylcyclohexenes, are versatile building blocks for the synthesis of pharmaceuticals and natural products. Despite the prevalence of these structural motifs, the development of efficient synthetic methods remains an unmet challenge. Herein we report a novel desymmetric isomerization of exocyclic olefins using a series of newly designed chiral cobalt catalysts, which enables a straightforward construction of chiral 1-methylcyclohexenes with diversified functionalities. The synthetic utility of this methodology is highlighted by a concise and enantioselective synthesis of a natural product, β-bisabolene. The versatility of the reaction products is further demonstrated by multifarious derivatizations.
The enantioselective intramolecular Morita-Baylis-Hillman reaction catalyzed by amino acid-derived phosphinothiourea
Gong, Jing-Jing,Yuan, Kui,Song, Hong-Liang,Wu, Xin-Yan
experimental part, p. 2439 - 2443 (2010/06/12)
A series of chiral bifunctional phosphinothioureas derived from l-amino acids have been developed to promote the enantioselective intramolecular Morita-Baylis-Hillman reaction. The process afforded the cyclic hydroxyl enones with up to 84% ee and good yields under mild conditions.
Absorption, Circular Dichroism, and Nuclear Magnetic Resonance Studies of Bis(acetylacetonato)cobalt(III) Complexes Containing 2-Aminoalkylphosphine Chelates with Phosphorus and Nitrogen Donor Atoms
Kashiwabara, Kazuo,Kinoshita, Isamu,Ito, Tasuku,Fujita, Junnosuke
, p. 725 - 732 (2007/10/02)
Bis(acetylacetonato)cobalt(III) complexes containing a variety of 2-aminoalkylphosphines, NH2CH2CH2P(C6H5)2, (CH3)2NCH2CH2P(C6H5)2, (S)-NH2CH(CH3)CH2P(C6H5)2, rac-NH2CH2CH2P(CH3)(C6H5), (R)-NH2CH2CH2P(C4H9)(C6H5) and NH2CH2CH2P(CH3)2, and a diphosphine, (C6H5)2PCH2CH2P(C6H5)2 were prepared and resolved (or separated) into optical isomers by SP-Sephadex column chromatography.Absorption, circular dichroism, and 1H and 13C NMR spectra of the new complexes were measured and the results compared with those of the related complexes.Positions of the 2-aminoalkylphosphine and the related ligands in the spectrochemical series were as follows; CN- > NH2CH2CH2P(CH3)2 > (C6H5)2PCH2CH2P(C6H5)2 > NH2CH2CH2P(CH3)(C6H5) NH2CH2CH2P(C4H9)(C6H5) > NH2CH(CH3)CH2P(C6H5)2 NH2CH2CH2P(C6H5)2 NH2CH2CH2NH2 > (CH3)2NCH2CH2P(C6H5)2.For the 13C NMR spectra, all the signals including those due to two diastereotopic phenyl groups on a phosphorus atom were assigned, and the chemical shifts and the coupling constants were determined.The methyl and carbonyl carbons which are trans to a phosphorus atom give a doublet signal due to four-bond (4J(C,P) = 6-7 Hz) and three-bond 3J(C,P) = 2-3 Hz) couplings, respectively, through a cobalt(III) ion.
