67404-97-1Relevant academic research and scientific papers
Tandem Blaise/retro-Blaise reaction for the nitrile-mediated regioselective intermolecular addition of unstabilized zinc ester enolates (Reformatsky Reagents) to 1-alkynes and 1,3-enynes
Kim, Ju Hyun,Chun, Yu Sung,Lee, Sang-Gi
, p. 11483 - 11493 (2013/12/04)
We report the novel use of a nitrile as a mediator to achieve the regioselective intermolecular addition of unstabilized zinc ester enolates (Reformatsky reagents) to 1-alkynes and 1,3-enynes. This reaction is made possible by a reversible addition of enolates to a nitrile (Blaise reaction), generating a zinc aza-enolate that, unlike zinc ester enolates, can add intermolecularly to 1-alkynes and 1,3-enynes. Subsequent removal of the nitrile through a retro-Blaise reaction generates the targeted addition product. This method is combined with a Diels-Alder reaction and subsequent oxidative aromatization, providing a tandem one-pot de novo construction of α-arylated alkanoates from Reformatsky reagents.
Highly selective nickel-catalyzed methyl-carboxylation of homopropargylic alcohols for α-alkylidene-γ;-butyrolactones
Li, Suhua,Ma, Shengming
supporting information; experimental part, p. 6046 - 6049 (2012/01/06)
A first practical Ni(0)-catalyzed highly stereoselective methyl-carboxylation of homopropargylic alcohols with ZnMe2 and CO2 for the efficient synthesis of α-alkylidene-γ;- butyrolactones is described. The reaction may be applied to
A BREAKTHROUGH FOR THE PHOTOCHEMICAL ARYLATION IN THE 3-(PHENYLMETHYL)-2(5H)-FURANONE SYSTEM LEADING TO THE TETRAHYDROINDENOFURANONE SYSTEM
Muraoka, Osamu,Tanabe, Genzoh,Sano, Kyohko,Momose, Takefumi
, p. 1093 - 1096 (2007/10/02)
The photochemistry of the 'central methane'-substituted 3-benzyl-2(5H)-furanone system (1) is described.Despite its di-?-methane structure, photochemical arylation was found to predominate in place of the di-?-methane rearrangement, and gave substituted t
Synthetic applications of 6-hydroxy-1-arylhexane-1,3-diones
De, Dibyendu,Seth, M.,Bhaduri, A. P.
, p. 503 - 506 (2007/10/02)
Facile synthesis of (E)-2-(aroylmethylene)tetrahydrofurans (17-19), 3-aryl-5-(γ-hydroxypropyl)isoxazoles (5-7), 6-hydroxy-1-aryl-3-substitutedaminohex-2-ene-1-ones (14-16), 3-cyano-6-hydroxy-1-arylhex-2-ene-1-ones (23-25) and one pot synthesis of 2-(α-phe
A Two-Step Preparation of α-Alkylidene γ-Lactones from γ-Lactones: A Synthesis of (+/-)-Ancepsenolide
Larson, Gerald L.,Perez, Rosa M. Betancourt de
, p. 5257 - 5260 (2007/10/02)
γ-Butyrolactone, γ-valerolactone, and the cis lactone of 2-hydroxycyclohexaneacetic acid have been C-silylated via their respective lithium enolates with diphenylmethylchlorosilane.The resulting α-silylated γ-lactones can be deprotonated and condensed with aldehydes and ketones to give α-alkylidene γ-lactones in moderate to excellent yield.The enolate of the α-diphenylmethylsilyl cis lactone of 2-hydroxycyclohexaneacetic acid condensed with 1-butanal but not with benzaldehyde or acetaldehyde.
New Methods for Stereoselective Synthesis of α-Alkylidene-γ-butyrolactones Using Monoanion of O-Ethyl S-(Tetrahydro-2-oxo-3-furanyl) Thiocarbonate and Dianion of α-Mercapto-γ-butyrolactone
Tanaka, Kazuhiko,Uneme, Hideki,Yamagishi, Nobuyuki,Tanikaga, Rikuhei,Kaji, Aritsune
, p. 2910 - 2916 (2007/10/02)
The lithium enolates of O-ethyl S-(tetrahydro-2-oxo-3-furanyl) dithiocarbonate and thiocarbonate were found to be efficient reagents for the stereoselective synthesis of α-alkylidene-γ-butyrolactones from carbonyl compounds.The dianion of α-mercapto-γ-butyrolactone was successfully generated by treatment of α-mercapto-γ-butyrolactone with 2.2 equivalents of lithium diisopropylamide in the presence of N,N,N',N'-tetramethylethylenediamine at -78 deg C in THF.The dianion thus formed has been utilized for the efficient and stereoselective synthesis of α-alkylidene-γ-butyrolactones from carbonyl compounds.
