259227-39-9Relevant academic research and scientific papers
Lanthanide (III) promoted aldol condensation of enones and aldehydes
Hong, Bor-Cherng,Chin, Sheng-Fei
, p. 1191 - 1197 (1997)
The first lanthanide (III) mediated α'-alkylation of MVK with aldehydes is described. This methodology allows the efficient preparation of a number of synthetically important hydroxyenones.
A short and flexible route to tetrahydropyran-4-ones via conjugated nitrile oxides cycloaddition and oxa-Michael cyclization: A concise diastereoselective total synthesis of (±)-diospongin A
Yao, Hongliang,Ren, Jingyun,Tong, Rongbiao
supporting information, p. 193 - 195 (2013/02/23)
A short and flexible [3+2+1] synthetic strategy was developed for the synthesis of substituted tetrahydropyran-4-ones, featuring [3+2]-cycloaddition of α,β-unsaturated nitrile oxides and alkenes and oxa-Michael cyclization in a 6-endo-trig fashion. The efficiency of this synthetic strategy was further demonstrated by the concise total synthesis of (±)-diospongin A in 8 steps with 20.2% yield. This journal is The Royal Society of Chemistry.
Oxidative Cyclization of β-Hydroxyenones with Palladium(II): A Novel Entry to 2,3-Dihydro-4H-pyran-4-ones
Reiter, Maud,Ropp, Sandrine,Gouverneur, Veronique
, p. 91 - 94 (2007/10/03)
(Equation presented) A palladium(II)-mediated oxidative cyclization was found to be effective for the preparation of structurally diverse 2,3-dihydro-4H-pyran-4-ones from the corresponding β-hydroxyenones. Attractive features of this transformation includ
Experiments directed towards the synthesis of anthracyclinones. XXXIV hetero-diels-alder reactions using chiral boron and titanium reagents
Bereich, Mark D.,Gambie, Richard C.,Rutledge, Peter S.
, p. 851 - 859 (2007/10/03)
Reactions between benzaldehyde or o-anisaldehyde and a series of silyloxy dienes catalysed by the chiral acyloxyborane (CAB) complex (4) give high yields of enantioselective products from a Mukaiyama aldol rather than a hetero-Diels-Alder reaction. Attempts to effect a similar catalytic reaction with anthraquinone aldehydes were unsuccessful but use of 2 equiv. of the CAB complex (1) followed by cyclization promotes a formal heteroDiels-Alder reaction between the aldehyde (7) and the diene (12) to give the dihydropyrone (24) in 45% yield and with a 79% e.e. in favour of the 2′R enantiomer. Hetero-Diels-Alder reactions between the aldehyde (7) and the diene (12) using the chiral titanium complexes Ti[(R)-BINOL]Cl2, Ti[(R,R)-TADDOL]Cl2 and Ti[(R)-BINOL]2 have been investigated. The first two complexes promote the reaction at -30 and -78° respectively but with low induced enantioselectivities.
