4728-91-0Relevant academic research and scientific papers
Relay-Heck Cross-Coupling Between Alkenyl Halides and Unsaturated Alcohols in the Synthesis of Open-Chain Analogues of Musk Odorant Vulcanolide
Lenormand, Anthony,Reyes Méndez, Lucía,Coulomb, Julien
supporting information, p. 9276 - 9280 (2021/05/28)
Unactivated alkenyl iodides and bromides underwent an unprecedented palladium-catalyzed relay-Heck cross-coupling with a whole range of alkenols of different chain lengths linking the alkene and the alcohol, affording unsaturated aldehydes and ketones in moderate to good yields. In contrast, alkenyl triflates were not suitable partners for this reaction. This method allowed the preparation of open-chain analogues of the musk odorant Vulcanolide, several of which retained key olfactory properties of the parent molecule.
Cyclobutyl phenyl sulfoxide and (SR)-cyclobutyl p-tolyl sulfoxide: New reagents for the spiroannelation of cyclopentanone
Fitjer, Lutz,Schlotmann, Werner,Noltemeyer, Mathias
, p. 4985 - 4988 (2007/10/02)
Cyclobutyl phenyl sulfide 2, cyclobutyl phenyl sulfoxide 3 and (SR)- cyclobutyl p-tolyl sulfoxide (SR)-8 have been synthesized and used for the spiroannelation of cyclopentanone. In the most effective sequence, lithiated 3 is added to ketones with formation of β-hydroxy sulfoxides 4a-g, which are ring enlarged and hydrolyzed to cyclopentanones 6a-e and sulfanylcyclopentene 6f, respectively, after reduction to β-hydroxy sulfides 5a-f. In an asymmetric version using (SR)-8, partial racemization during ring enlargement was observed.
Intramolecular Nucleophilic Acyl Substitution Reactions of Halo-Substituted Esters and Lactones. New Applications of Organosamarium Reagents
Molander, Gary A.,McKie, Jeffrey A.
, p. 7216 - 7227 (2007/10/02)
Intramolecular nucleophilic acyl substitution reactions involving a broad range of halo substituted carboxylic acid derivatives have been accomplished in excellent yield employing samarium(II) iodide as the reductive coupling agent.Although particular substrates cyclized most effectively in THF in the presence of tripiperidinophosphine oxide, carboxylic acid esters, the focus of this report, cyclize equally well without such an additive in the presence of a catalytic quantity of iron(III) complexes.Thus a comprehensive series of halo substituted esters were cyclized in excellent yield to the corresponding 4-, 5-, and 6 -membered carbocycles.The reaction is extremely mild and selective as demonstrated by experiments wherein alkyl chlorides, acetals, and olefins remain completely intact under the reaction conditions.In addition to introducing a convenient procedure for preparing stereodefined spirocyclic systems, a new ring expansion sequence has been developed that appears extremely general for the preparation of various ring systems.
A Cyclopentanone Annulation via Intramolecular Acylation of Alkylsilanes
Urabe, Hirokazu,Kuwajima, Isao
, p. 1140 - 1141 (2007/10/02)
A facile construction of cyclopentanones is achieved via ring closure of 5-(trimethylsilyl)alkanoyl chlorides under the influence of AlCl3.
Intramolecular Sulfur Ylide Additions to Ketones
Crandall, Jack K.,Magaha, H. Steve,Henderson, Mark A.,Widener, Rexford K.,Tharp, Gregg A.
, p. 5372 - 5380 (2007/10/02)
Methodology is described for the annulation of five-membered carboxylic rings onto cycloalkanones, using an intramolecular sulfur ylide reaction.Epoxybicycloalkanes (x = 3, 4, 5, 6) were obtained from cycloalkanones via the corresponding 2-3-(phen
INTRAMOLECULAR SULFOR-YLIDE ADDITIONS TO KETONES. A CYCLOPENTANE ANNULATION
Crandall, J. K.,Magaha, H. S.,,Widener, R. K.,Tharp, G. A.
, p. 4807 - 4810 (2007/10/02)
Various 2-(3'-phenylthiopropyl)cycloalkanones were prepared from the corresponding ketones and subjected to S-alkylation by triethyloxonium tetrafluoroborate followed by potassium tert-butoxide treatment to give bicyclic epoxides with new five-membered ca
