740816-35-7Relevant academic research and scientific papers
Enantioselective formation of quaternary stereocenters using the catalytic intramolecular Stetter reaction
Moore, Jennifer L.,Kerr, Mark S.,Rovis, Tomislav
, p. 11477 - 11482 (2007/10/03)
Asymmetric formation of quaternary stereocenters has been accomplished using the catalytic intramolecular Stetter reaction. A?variety of tethered aldehydes and Michael acceptors are cyclized in excellent yields and enantioselectivities.
Enantioselective alkylations of tributyltin enolates catalyzed by Cr(salen)CI: Access to enantiomerically enriched all-carbon quaternary centers
Doyle, Abigail G.,Jacobsen, Eric N.
, p. 62 - 63 (2007/10/03)
The catalytic asymmetric α-alkylation of tributyltin enolates with a range of primary alkyl halides is catalyzed by a chiral Cr(salen) complex. The reaction constitutes the first transition-metal-catalyzed system for α-alkylation of carbonyl substrates wi
Enantioselective synthesis of quaternary stereocenters via a catalytic asymmetric stetter reaction
Kerr, Mark S.,Rovis, Tomislav
, p. 8876 - 8877 (2007/10/03)
A new electron-deficient chiral triazolium salt has been shown to catalyze the formation of quaternary stereocenters by an asymmetric intramolecular Stetter reaction. Pentafluorophenyl substitution on an aminoindanol-derived catalyst affords tertiary ether, thioether, and quaternary stereocenters in typically greater than 90% ee and very good chemical yield. Aromatic and aliphatic aldehydes are equally competent substrates for this reaction. The reaction proceeds at room temperature under mild conditions to provide quaternary stereocenters with functional group relationships that are particularly difficult to access by other methods. Copyright
Nitroalkenes as electrophiles in the asymmetric Michael reaction involving chiral imines/enamino esters
Thominiaux, Cyrille,Rousse, Sebastien,Desmaele, Didier,D'Angelo, Jean,Riche, Claude
, p. 2015 - 2021 (2007/10/03)
Addition of 2-nitropropene to the chiral imine derived from 2- methylcyclopentanone and (S)-1-phenylethylamine furnished the expected Michael adduct. The latter compound was then efficiently converted into (R)- pentalenone through a Nef reaction. Condensa
Carbonyl-Protected β-Lithio Aldehydes and Ketones via Reductive Lithiation. A General Preparative Method for Remarkably Versatile Homoenolate Equivalents
Cherkauskas, John P.,Cohen, Theodore
, p. 6 - 8 (2007/10/02)
A general procedure for producing homoenolate equivalents consists of reductive lithiation, induced by 4,4'-di-tert-butylbiphenylide, of carbonyl-protected β-(phenylthio) carbonyl compounds prepared in turn by thiophenol addition to enones or the alkylati
MICHAEL REACTION OF SILYL ENOL ETHERS OR KETENE SILYL ACETALS WITH CONJUGATED NITRO OLEFINS ACTIVATED BY THE LEWIS ACID: NEW SYNTHESIS OF 1,4-DIKETONES AND gamma -KETO ESTERS.
Miyashita,Yanami,Kumazawa,Yoshikoshi
, p. 2149 - 2156 (2007/10/02)
New one-pot procedures for the synthesis of 1,4-diketones and gamma -keto esters utilizing conjugated nitro olefins are described. Reaction of silyl enol ethers with aliphatic nitro olefins in the presence of a Lewis acid affords 1,4-diketones in good yie
Stereoselective Total Syntheses of(+/-)-Gymnomitrol and (+/-)-Gymnomitrene
Welch, Steven C.,Chayabunjonglerd, Suthep,Rao, A.S.C.Prakasa
, p. 4086 - 4093 (2007/10/02)
Stereoselective total syntheses of (+/-)-gymnomitrol (2A) and (+/-)-gymnomitrene (2B)in 12 synthetic stages each from 2-methylcyclopentanone (3)are presented.The key features of these syntheses are (a)the conjugate addition of lithium dimethylcopper to enone 8 followed by alkylation of the intermediate enolate anion with allyl chloride to afford ketone 9, (b) stereoselective alkylation of ketone 9,(c) a modified intramolecular Claisen condensation and enolate anion trapping with tert-butyldimethylsilyl chloride to give tricyclic ketone 14B, and (d) convenient utilization of a common intermediate in the construction of both natural products 2A and 2B by sequential chemical manipulation of 15A followed by desilylation to produce either ketone 16 or 18 in one-pot reactions.
