75649-59-1Relevant academic research and scientific papers
Further Studies on the Direct Synthesis of α,β-Unsaturated Ketimines and α,β-Enones by Chemoselective Dehydrative Addition of Functionalized Alkenes to Secondary Amides
Huang, Pei-Qiang,Huang, Ying-Hong
, p. 613 - 620 (2017)
Described in this paper are the results of an investigation on the extension of the C-H alkyliminylation and acylation of alkenes with secondary amides. The nucleophilic partner has been extended to cover a series of functionalized alkenes bearing functional groups including ester, α,β-unsaturated ester, uncongested ketone groups, as well as enol derivatives of acetaldehyde such as enol ether and enamides. The electrophilic partner has been extended from N-(2,6-dimethylphenyl) and N-methyl amides to N-n-butyl, and N-cyclohexyl amides. The results demonstrated that the method can be used to synthesize a number of functionalized α,β-unsaturated ketimines and α,β-enones in an efficient, high yielding, and one-pot manner. The method was applied to a concise synthesis of (E)-6-styryltetrahydro-2H-pyran-2-one (5), an immediate intermediate in the syntheses of a series of styryllactone natural products including (±)-goniothalamine (6), (±)-goniothalamine oxide (7), (±)-goniodiol (8), (±)-leiocarpin A (9), (±)-9-deoxygoniopypyrone (10), and (±)-7-epi-goniodiol (11).
From vinyl pyranoses to carbasugars by an iron-catalyzed reaction complementary to classical Ferrier carbocyclization
Mac, Dinh Hung,Samineni, Ramesh,Petrignet, Julien,Srihari, Pabbaraja,Chandrasekhar, Srivari,Yadav, Jhillu Singh,Gree, Rene
supporting information; experimental part, p. 4717 - 4719 (2010/01/16)
Starting from vinyl pyranoses an iron-catalyzed tandem isomerization- intramolecular aldolization reaction was developed to prepare cyclohexenone derivatives bearing substituents on the double bond, and it has been applied in a short synthesis of 4-epi-ga
Suppression of β-hydride elimination in the intramolecular hydrocarboxylation of alkynes leading to the formation of lactones
Huo, Zhibao,Patil, Nitin T.,Jin, Tienan,Pahadi, Nirmal K.,Yamamoto, Yoshinori
, p. 680 - 684 (2008/02/09)
Palladium-catalyzed intramolecular cyclization of the alkynoic acids was studied which gave the five- and six-membered lactones in moderate yields. The reaction can be conducted simply by heating a toluene solution of alkynoic acids at 100 °C in the prese
Alkynes as activators in the nickel-catalysed addition of organoboronates to aldehydes
Takahashi, Go,Shirakawa, Eiji,Tsuchimoto, Teruhisa,Kawakami, Yusuke
, p. 1459 - 1461 (2007/10/03)
Alkynes act not as substrates but as co-catalysts in the presence of a nickel catalyst, an organoboronate and an aldehyde to promote the addition reaction between the substrates in combination with H2O. The Royal Society of Chemistry 2005.
SYNTHESIS OF VINYLIC LACTONES VIA PALLADIUM-CATALYZED COUPLING OF VINYLIC HALIDES OR TRIFLATES AND UNSATURATED CARBOXYLIC ACIDS
Larock, Richard C.,Leuck, David J.,Harrison, L. Wayne
, p. 6399 - 6402 (2007/10/02)
Vinylic halides or triflates react with 3-butenoic or 4-pentenoic acids in the presence of 5percent Pd(OAc)2 or Pd(dba)2, n-Bu4NCl, i-PrNEt and either acetonitrile or N,N-dimethylformamide at 80-100 deg C to afford the corresponding γ-alkenyl-γ-butyro- or
