762-47-0Relevant academic research and scientific papers
Unexpected cycloisomerizations of nonclassical carbocation intermediates in gold(I)-catalyzed homo-rautenstrauch cyclizations
Wang, Guan,Zou, Yue,Li, Zhiming,Wang, Quanrui,Goeke, Andreas
, p. 5825 - 5831 (2011/09/12)
An unexpected gold(I)-catalyzed homo-Rautenstrauch rearrangement of 1-cyclopropyl propargylic esters to cyclohexenones is disclosed. This rearrangement represents new evidence for the recently discussed gold-stabilized nonclassical carbocation character of intermediates in gold catalysis. A mechanistic study proved partial chirality transfer from optically active propargyl acetates.
Preparation of bicyclic 1,2,4-trioxanes from γ,δ-unsaturated ketones
Ramirez, Armando P.,Thomas, Andrew M.,Woerpel
supporting information; experimental part, p. 507 - 510 (2009/08/07)
(Chemical Equation Presented) Treatment of γ,δ-unsaturated ketones with hydrogen peroxide and acid provides a rapid entry into the medicinally important 1,2,4-trioxane structure. Alkene substitution that stabilizes carbocationic intermediates proved to be important for the success of this transformation.
Pd-catalyzed ring opening of cyclopropanols
Okumoto, Hiroshi,Jinnai, Takamitsu,Shimizu, Hiroyuki,Harada, Yoshinori,Mishima, Hideki,Suzuki, Akira
, p. 629 - 630 (2007/10/03)
Treatment of substituted cyclopropanols with a Pd catalyst in MeCN at 50 °C gave enones in good yields.
A new route to trans 2,5-dialkylpyrrolidines
Dumas, Franoise,D'Angelo, Jean
, p. 2005 - 2008 (2007/10/02)
Benzylic amines 8 react with ketoenoates 7 yielding, after reduction of the primary adducts, 2,5-dialkylpyrrolidines 9 (trans isomer predominating). This reaction has been applied to the synthesis of trans 2-heptyl-5-ethylpyrrolidine, a component of the venom of fire ant (Solenopsis punctaticeps).
Synthesis of 2-Alkyl-2-cyclopenten-1-ones. A Versatile Kinetic Alkylation-Ozonolysis Procedure for the Preparation of γ-Ketoaldehydes
Geraghty, Niall W. A.,Morris, Noreen M.
, p. 603 - 607 (2007/10/02)
A range of 2-alkyl-2-cyclopenten-1-ones including the prostaglandin precursor 2-(6-methoxycarbonylhexyl)-2-cyclopenten-1-one and the jasmonoid precursor 2--2-cyclopenten-1-one, have been prepared by a short synthetic route which begins with 6-methyl-5-hepten-2-one and generates the key 1,4-ketoaldehyde intermediates by a kinetic alkylation-ozonolysis procedure.
Synthesis of (Z,E)- and (Z,Z)-α-Farnesenes and -Homofarnesenes
Morgan, E. David,Thompson, Lorna D.
, p. 399 - 404 (2007/10/02)
The ant substance (Z,E)-α-farnesene and its isomer (Z,Z)-α-farnesene have been synthesized in an overall yield of 34percent in six stages from methyl cyclopropyl ketone and 6-methylhept-5-en-2-one via a Wittig condensation.A mixture of the corresponding (Z,E)-α-homofarnesene of ants and its (Z,Z) isomer were prepared in much poorer yield by the same method and incompletely characterized.The isomeric identification of both insect materials were confirmed.
Ultrasound in Organic Synthesis. 7. Preparation of Organozinc Reagents and Their Nickel-Catalyzed Reactions with α,β-Unsaturated Carbonyl Compounds
Petrier, Christian,Barbosa, Jayne C. de Souza,Dupuy, Claude,Luche, Jean-Louis
, p. 5761 - 5765 (2007/10/02)
Diorganozinc compounds can be prepared with great ease and efficiency in a one-pot process, by sonication of lithium, an organic halide, and a zinc halide in THF or toluene mixtures.The reagents thus obtained give rise to clean and selective conjugate additions to α,β-unsaturated aldehydes and ketones in the presence of catalytic amounts of nickel acetylacetonate.
