127253-15-0Relevant articles and documents
A phosphine-free iron complex-catalyzed synthesis of cycloalkanes: Via the borrowing hydrogen strategy
Bettoni, Léo,Gaillard, Sylvain,Renaud, Jean-Luc
supporting information, p. 12909 - 12912 (2020/11/07)
Herein we report a diaminocyclopentadienone iron tricarbonyl complex catalyzed synthesis of substituted cyclopentane, cyclohexane and cycloheptane compounds using the borrowing hydrogen strategy in the presence of various substituted primary and secondary 1,n diols as alkylating reagents. Deuterium labeling experiments confirm that the diols were the hydride source in this cascade process. This journal is
STEREOSELECTIVE SYNTHESIS OF 3,4-DISUBSTITUTED CYCLOPENTANONES AND RELATED COMPOUNDS
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Page/Page column 46-47, (2010/11/25)
Methods and materials for preparing optically active 3,4-disubstituted cyclopentanones are disclosed. The method includes hydrolyzing one or more compounds represented by Formula (13), or removing an ester moiety from a compound represented by Formula (18).
An approach to the imine ring system of pinnatoxins
Pelc, Matthew J.,Zakarian, Armen
, p. 1629 - 1631 (2007/10/03)
(Chemical Equation Presented) A concise stereoselective approach to the spirobicyclic imine fragment of pinnatoxins and pteriatoxins is described. The approach relies on a tandem reaction sequence involving consecutive sigmatropic rearrangements to build
Enantioselective vicinal bis-acylation of olefins
Ghosez, Leon,Mahuteau-Betzer, Florence,Genicot, Christophe,Vallribera, Adelina,Cordier, Jean-Francois
, p. 3411 - 3422 (2007/10/03)
A two-step sequence for the asymmetric vicinal acylation of olefins by a [2+2+1] strategy is reported. The key reaction is a [2+2] cycloaddition of an olefin to a chiral keteniminium salt derived from N-tosylsarcosinamide. This is followed by a regioselec
Enantioselective diene cyclization/hydrosilylation catalyzed by optically active palladium bisoxazoline and pyridineoxazoline complexes
Perch, Nicholas S.,Pei, Tao,Widenhoefer, Ross A.
, p. 3836 - 3845 (2007/10/03)
A 1:1 mixture of (N-N)Pd(Me)Cl [N-N = (S,S)-4,4'-dibenzyl-4,5,4',5'- tetrahydro-2,2'-bisoxazoline] (S,S-4a) and NaBAr4 [Ar = 3,5-C6H3(CF3)2] (5 mol %) catalyzed the asymmetric cyclization/hydrosilylation of dimethyl diallylmalonate (2) and triethylsilane at -30 °C for 48 h to form an 8.1:1 mixture of the silylated carbocycle (S,S)-trans-1,1-dicarbomethoxy-4-methyl- 3-[(triethylsilyl)methyl]cyclopentane (S,S-3) (95% de, 72% ee) and dimethyl 3,4-dimethylcyclopentane-1,1-dicarboxylate (S,S-6) in 64% combined yield. In comparison, a 1:1 mixture of the palladium pyridineoxazoline complex (N- N)Pd(Me)Cl [N-N = (R)-(+)-4-isopropyl-2-(2-pyridinyl)-2-oxazoline] (R-5b) and NaBAr4 (5 mol %) catalyzed the asymmetric cyclization/hydrosilylation of 2 and triethylsilane at -32 °C for 24 h to form carbocycle S,S-3 in 82% yield (>95% de, 87% ee) as the exclusive product. Asymmetric diene cyclization catalyzed by complex R-5b was compatible with a range of functional groups and produced carbocycles with up to 91% ee. The procedure also tolerated substitution at a terminal olefinic position and at the allylic position of the diene.
Asymmetric synthesis of 1,3- and 1,3,4-substituted pyrrolidines
Lin, Jing,Chan, Wing Hong,Lee, Albert W. M.,Wong, Wai Yeung,Huang, Pei Qiang
, p. 2949 - 2951 (2007/10/03)
Diastereoselective alkylation of N-acylnorbornene sultams 2 afforded a variety of enantiomerically pure products 3a-3e. Reduction with LiAlH4 (LAH) followed by ditosylation furnished chiral 1,4-ditosylates 5a-5e which underwent a cyclization reaction with primary amines to afford chiral 1,3- and 1,3,4-substituted pyrrolidines. (C) 2000 Elsevier Science Ltd.
Asymmetric vicinal acylation of olefins: A new approach to enantiomerically pure γ-lactones
Genicot,Ghosez
, p. 7357 - 7360 (2007/10/02)
Amide 3 derived from N-tosylsarcosine and (2R,5R)-dimethylpyrrolidine was converted into keteniminium salt 4 which readily cycloadded to olefins. Hydrolysis of the adducts yielded cyclobutanones which were regiospecifically oxidized to γ-lactones 7. High
ASYMMETRIC 1,4-ADDITIONS TO γ-MENTHYLOXYBUTENOLIDES. ENANTIOSPECIFIC SYNTHESIS OF CHIRAL 1,4-BUTANEDIOLS.
Jansen, Johan F.G.A.,Feringa, Ben L.
, p. 5481 - 5484 (2007/10/02)
Optically active methyl-substituted butanediols and γ-lactones were prepared from γ-menthyloxy-2--furanone.