Inductive and Resonance Effects of Substituents on π-Face Selection

Cieplak, Andrzej Stanislaw

doi:10.1021/cr980381n

Cited by 144 publications

(66 citation statements)

References 390 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The strans diene system in 3 is incorporated into a system containing a six-membered ring. To exclude specific effects in such systems, such as in the reduction of cyclohexanones [14] or in S N 2Ј reactions, [15] we tried to prepare dienes 7 and 10 ( Figure 2) and to submit these compounds to the oxidative cyclization reaction. Each isomer should lead to a single hydroxy lactone (8 and 11, respectively).…”

Section: Resultsmentioning

confidence: 99%

Studies on an Oxidative 1,4‐Addition to s‐trans‐1,3‐Dienes, a Key Reaction in a Strigol Total Synthesis

et al. 2003

View full text Add to dashboard Cite

Keywords: Oxidation / Olefination / Palladium / StereochemistryOxidation of 4,6-heptadienoic acid systems with hydrogen peroxide in the presence of a catalytic amount of diphenyl diselenide leads to 5-(3-hydroxypropenyl)dihydrofuran-2-one systems with defined relative configuration at the 4 and 7 positions (carboxylic acid numbering). A system having a six-membered ring as part of the s-trans-diene system was an intermediate in a strigol total synthesis; a second system lacking the six-membered ring is the subject of the present publication. We accomplished a stereoselective synthesis of

show abstract

Section: Resultsmentioning

confidence: 99%

Studies on an Oxidative 1,4‐Addition to s‐trans‐1,3‐Dienes, a Key Reaction in a Strigol Total Synthesis

et al. 2003

View full text Add to dashboard Cite

show abstract

“…13 C NMR spectra were recorded at 75 MHz; chemical shifts are given relative to a solvent resonance. NOE data are presented in this form: Saturated signal (enhanced signal, enhancement).…”

Section: Methodsmentioning

confidence: 99%

“…NOE data are presented in this form: Saturated signal (enhanced signal, enhancement). The number of carbons in the signal and the number of attached hydrogens, based on DEPT and heteronuclear correlation spectra, are given in parentheses following each 13 …”

Section: Methodsmentioning

confidence: 99%

“…These were separated by flash chromatography. Supporting Information (see footnote on the first page of this article): Assignments of 1 H NMR spectra, NOE data, MS data, 1 H and 13 C NMR spectra, computed energies, and Cartesian coordinates.…”

Section: Diels-alder Reaction With 23mentioning

confidence: 99%

“…[12] However, an alternative view was that the facial selectivity is controlled by delocalization of the anti σ orbital into the incipient σ* orbital. [13] Dienophiles 6 and 7 are clearly geometrically similar to dienes 4 and 5. In the endo transition states, the steric interactions of 6 and 7 with a simple diene should be similar to those experienced by 4 and 5 with an ethylenic dienophile, and so the facial selectivities of 6 and 7 should be similar to those of 4 and 5 if steric hindrance is the only major controlling factor in the Diels-Alder reactions.…”

Section: Introductionmentioning

confidence: 95%

See 2 more Smart Citations

Facial Selectivity in the Diels–Alder Reactions of 2,2‐Disubstituted Cyclopent‐4‐ene‐1,3‐dione Derivatives and a Computational Examination of the Facial Selectivity of the Diels–Alder Reactions of Structurally Related Dienes and Dienophiles

Liu¹,

Wu²,

Pye³

et al. 2011

Eur J Org Chem

View full text Add to dashboard Cite

Intra- and Intermolecular Hydrogen Bonding Effects in Cycloadditions between Nitrile Oxides and 4-Benzoylamino-2-cyclopenten-1-ol and Its Derivatives

et al. 2002

View full text Add to dashboard Cite

Keywords: Cycloadditions / Nitrile oxides / Nitroso compounds / Solvent effects / StereoselectivityCycloadditions between nitrile oxides and cis-4-benzoylamino-2-cyclopenten-1-ol offer an example in which a strong intramolecular hydrogen bond completely offsets the syn-directing ability of the cyclopentene substituents. Solvents affected the conformational equilibrium of the cyclopentene dipolarophile but did not sizeably influence the cycloaddition selectivity, showing the absence of directing effects between

show abstract

Inductive and Resonance Effects of Substituents on π-Face Selection

Cited by 144 publications

References 390 publications

Studies on an Oxidative 1,4‐Addition to s‐trans‐1,3‐Dienes, a Key Reaction in a Strigol Total Synthesis

Studies on an Oxidative 1,4‐Addition to s‐trans‐1,3‐Dienes, a Key Reaction in a Strigol Total Synthesis

Facial Selectivity in the Diels–Alder Reactions of 2,2‐Disubstituted Cyclopent‐4‐ene‐1,3‐dione Derivatives and a Computational Examination of the Facial Selectivity of the Diels–Alder Reactions of Structurally Related Dienes and Dienophiles

Intra- and Intermolecular Hydrogen Bonding Effects in Cycloadditions between Nitrile Oxides and 4-Benzoylamino-2-cyclopenten-1-ol and Its Derivatives

Contact Info

Product

Resources

About