Synthesis of gamma-Lactones and 3-Alkylidene-1-indanones.

Jalander, Lars; Broms, Merete; Ortéga, Carmen; Samuelsson, Bertil; Enzell, Curt R.; Berg, Jan-Eric

doi:10.3891/acta.chem.scand.36b-0371

Cited by 11 publications

(4 citation statements)

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“…Purification by recrystallization (EA/PE) afforded the product as a white solid: yield 160 mg, 90%; 1 H NMR (400 MHz, CDCl 3 ) δ = 7.35–7.29 (m, 3H), 7.10–7.07 (m, 2H), 5.82 (d, J = 0.9 Hz, 1H), 2.28–2.22 (m, 1H), 1.80–1.75 (m, 4H), 1.26–1.10 (m, 6H); 13 C{ 1 H} NMR (100 MHz, CDCl 3 ) δ = 171.6, 167.0, 139.9, 127.7, 127.4, 127.0, 115.2, 47.7, 31.6, 26.4, 26.0; mp 140–142 °C. The analytical data are consistent with the literature …”

Section: Methodssupporting

confidence: 90%

Enantioselective Hydrogenation of β,β-Disubstituted Unsaturated Carboxylic Acids under Base-Free Conditions

et al. 2016

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An additive-free enantioselective hydrogenation of β,β-disubstituted unsaturated carboxylic acids catalyzed by the Rh-(R,R)-f-spiroPhos complex has been developed. Under mild conditions, a wide scope of β,β-disubstituted unsaturated carboxylic acids were hydrogenated to the corresponding chiral carboxylic acids with excellent enantioselectivities (up to 99.3% ee). This methodology was also successfully applied to the synthesis of the pharmaceutical molecule indatraline.

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Section: Methodssupporting

confidence: 90%

Enantioselective Hydrogenation of β,β-Disubstituted Unsaturated Carboxylic Acids under Base-Free Conditions

et al. 2016

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“…13 C NMR: δ 14.19, 55.53, 55.84, 60.19, 112.24, 113.06, 116.85, 118.78, 123.78, 139.56, 152.62, 153.33, 167.16. 1 H NMR and 13 C NMR spectra are in good agreement with the reported values of chemical shifts and coupling constants. 15a,d …”

Section: Methodssupporting

confidence: 86%

“…13 C NMR (CDCl 3 , 75 MHz): δ 20.70, 20.73, 27.04, 128.96, 130.52, 131.99, 136.41, 138.11, 141.54, 197.89. The structure of this compound was confirmed by converting it to ( Z )-[(2 E )-3-mesitylprop-2-enylidene]succinic anhydride,15e mp 159.6−162 °C (160.0−161 °C) 15e…”

Section: Methodsmentioning

confidence: 90%

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Novel Pd(II)- and Pt(II)-Catalyzed Regio- and Stereoselective trans-Hydroarylation of Alkynes by Simple Arenes

et al. 2000

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Efficient trans-hydroarylation of alkynes by simple arenes has been realized regio-and stereoselectively at room temperature in the presence of Pd(II) or Pt(II) catalysts and a mixed solvent containing trifluoroacetic acid (TFA). Various arenes undergo trans-hydroarylation selectively across terminal and internal C-C triple bondssincluding those conjugated to CHO, COMe, CO 2 H, and CO 2 Et groups, affording kinetically controlled cis-arylalkenes predominantly in most cases, especially, in good yields for electron-rich arenes and activated alkynes. The formation of arene/alkyne 1/2 or 2/1 adducts as side products is dependent on the arenes' and alkynes' substituents, which can be suppressed in some cases by changing the catalyst, catalyst concentration, and reaction time. The Pt(II) system, PtCl 2 /2AgOAc/TFA, shows lower catalytic activity than Pd(OAc) 2 /TFA, but higher selectivity, giving higher yields of adducts at the same conversion. On the basis of several isotope experiments and control reactions, a possible mechanism involving electrophilic metalation of aromatic C-H bonds by in-situ-generated cationic Pd(II) and Pt(II) species leading to intermolecular transarylpalladation to alkynes has been discussed.

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