344360-07-2Relevant academic research and scientific papers
Asymmetric IrI-catalysed allylic alkylation of monosubstituted allylic acetates with phosphorus amidites as ligands
Bartels, Bjoern,Garcia-Yebra, Cristina,Helmchen, Guenter
, p. 1097 - 1103 (2003)
Monodentate phosphorus amidites derived from 2,2′-binaphthol and a variety of chiral amines were employed as ligands in IrI-catalysed allylic alkylations of unsymmetrically substituted allylic acetates. The enantio- and regioselectivities of these reactions were investigated. Phosphorus amidites of bulky secondary chiral amines induced enantioselectivities of up to 94% ee in reactions of linear substrates. Phosphorus amidites derived from chiral primary amines, which have not been previously employed in asymmetric catalysis, furnished improved regioselectivities. The use of LiCl as additive led to improved regio- and enantioselectivities. ( Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003).
Ir-catalyzed asymmetric allylic alkylation using chiral diaminophosphine oxides: DIAPHOXs. Formal enantioselective synthesis of (-)-paroxetine
Nemoto, Tetsuhiro,Sakamoto, Tatsurou,Fukuyama, Takashi,Hamada, Yasumasa
, p. 4977 - 4981 (2008/02/09)
An Ir-catalyzed asymmetric allylic alkylation using chiral diaminophosphine oxide is described. Asymmetric allylic alkylation of terminal allylic carbonates proceeded using 5 mol % of Ir catalyst, 5 mol % of DIAPHOX 1i, 10 mol % of NaPF6, 10 mo
Carbocycles via enantioselective inter- and intramolecular iridium-catalysed allylic alkylations
Streiff, Stephane,Welter, Carolin,Schelwies, Mathias,Lipowsky, Gunter,Miller, Nicole,Helmchen, Guenter
, p. 2957 - 2959 (2007/10/03)
Carbocycles with > 90% ee were prepared via Ir-catalysed asymmetric allylic alkylation/ring closing metathesis sequences or enantioselective Ir-catalysed intramolecular allylic alkylations. The Royal Society of Chemistry 2005.
Iron tricarbonyl stabilized pentadienyl cation as initiator for cascade polycyclizations: A diastereoselective entry into octahydrophenanthrenes
Pearson, Anthony J.,Ghidu, Victor P.
, p. 8975 - 8978 (2007/10/03)
A new example is provided of completely diastereoselective polycyclization, affording the octahydrophenanthrene framework. Generation of an iron tricarbonyl stabilized pentadienyl carbocation is the triggering event of the cascade reaction. The carbocation is generated by anchimerically assisted regiospecific protonation of a double bond adjacent to the iron tricarbonyl diene moiety. Tetrafluoroboric acid ether complex appears to be the optimum reagent, affording good yields, even under catalytic conditions.
Regio- and enantioselective iridium-catalyzed allylic alkylation with in situ activated P,C-chelate complexes
Lipowsky, Gunter,Miller, Nicole,Helmchen, Guenter
, p. 4595 - 4597 (2007/10/03)
Come together: Successful cooperation of iridium and copper yielded a new catalyst system for allylic alkylation. Branched alkylation products can be obtained rapidly and with high enantioselectivity from simple linear precursors (see scheme; cod = cycloo
Pesticidal activity of functionalized alkenes
-
Page column 13-14, (2008/06/13)
The present invention provides non-peptide organic compounds that have a structure analogous to or reminiscent of the TMOF structure and have pesticidal activity. Thus the present invention concerns pesticidal compounds that inhibit digestion in pests by terminating or otherwise blocking synthesis of digestive enzymes by activating a TMOF receptor (collectively referred to herein as “pesticidal compounds”). The pesticidal compounds and other compounds of the present invention are usefully employed in the control of pests, particularly insect pests such as mosquitoes, which ingest blood.
High enantioselectivity in rhodium-catalyzed allylic alkylation of 1-substituted 2-propenyl acetates
Hayashi, Tamio,Okada, Atsushi,Suzuka, Toshimasa,Kawatsura, Motoi
, p. 1713 - 1715 (2007/10/03)
(Matrix presented) Rhodium-catalyzed asymmetric allylic alkylation of 1-substituted 2-propenyl acetates with dimethyl malonate proceeded with high enantioselectivity in the presence of cesium carbonate as a base and a rhodium catalyst generated from Rh(dp
Iridium-catalysed allylic substitution: Stereochemical aspects and isolation of IrIII complexes related to the catalytic cycle
Bartels, Bjoern,Garcia-Yebra, Cristina,Rominger, Frank,Helmchen, Guenter
, p. 2569 - 2586 (2007/10/03)
Ir-catalysed allylic alkylations of enantiomerically enriched monosubstituted allylic acetates proceed with up to 87% retention of configuration using P(OPh)3 as ligand. High retention enantioselectivity of up to 86% ee in asymmetric allylic alkylations of achiral or racemic substrates is achieved with monodentate phosphorus amidites as ligands. Lithium N-tosylbenzylamide was identified as a suitable nucleophile for allylic aminations. Of particular importance is the use of lithium chloride as an additive, generally leading to increased enantioselectivities. Two (π-allyl)IrIII complexes were characterised by X-ray crystal structure analysis and spectroscopic data.
Ir-catalysed allylic substitution: Mechanistic aspects and asymmetric synthesis with phosphorus amidites as ligands
Bartels, Bjoern,Helmchen, Guenter
, p. 741 - 742 (2007/10/03)
Ir-catalysed allylic alkylations of enantiomerically enriched monosubstituted allylic acetates proceed with up to 79% retention of configuration using P(OPh)3 as ligand; further evidence supports the assumption of σ-allyl complexes as intermediates, and high regio- and enantioselectivity in asymmetric allylic alkylations of achiral or racemic substrates is achieved with phosphorus amidites as ligands.
