Configuration and conformation of cis- and trans-3,5-dimethylvalerolactones

Carroll, F. Ivy; Mitchell, Gordon N.; Blackwell, Joseph T.; Sobti, Asha; Meck, R.

doi:10.1021/jo00940a020

Cited by 38 publications

(10 citation statements)

References 8 publications

(17 reference statements)

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“…tions in the steroid series,4 empirical correlations, arid single frequency off-resonance decoupling experiments. 5 As expected, the modification of ring D to a six-membered lactone ring does not alter the chemical shift of remote carbons (C-l to C-6, C-10, C-ll) relative to those in the parent steroid 5a-androstane derivative (1). The remaining carbons outside the lactone ring (C-7, C-8, C-9, and C-12) suffer minor changes of position of their respective resonances.…”

supporting

confidence: 60%

“…Ironically, even the regio-and stereospecificity of the reagent can be a disadvantage if the isomeric derivative is the one desired. We have sought a reaction sequence which (1) makes efficient use of scarce reagents, (2) produces cyclobutanones in good yields where the dichloroketene method does not, and (3) is stereospecific but in a complimentary sense to dichloroketene. This paper describes a technique for the large-scale, stereospecific, and high-yield preparation of a number of fused ring and polycyclic cyclobutanones from readily available starting materials.…”

Section: Received June 18 1975mentioning

confidence: 99%

See 1 more Smart Citation

Carbon-13 nuclear magnetic resonance spectroscopy of polycyclic .delta.-lactones

Gašić¹,

Ďjarmati²,

Pelletier³

1976

J. Org. Chem.

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supporting

confidence: 60%

Section: Received June 18 1975mentioning

confidence: 99%

Carbon-13 nuclear magnetic resonance spectroscopy of polycyclic .delta.-lactones

Gašić¹,

Ďjarmati²,

Pelletier³

1976

J. Org. Chem.

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“…The proton NMR was consistent with the cis isomer. 23 2-Methoxy-4,6-dimethyltetrahydropyran (5). The general method of Babcock et al was used.20 An ether solution of lithium aluminum hydride (37 mL, 1.7 M) was added dropwise under nitrogen to a stirred solution of 32.1 g of lactone 11 in 100 mL of dry ether at -5 °C over a 70-min period.…”

Section: Discussionmentioning

confidence: 99%

Anomeric effect in 2-alkoxytetrahydropyrans studied by carbon-13 and oxygen-17 NMR chemical shifts

McKelvey¹,

Kawada²,

Sugawara³

et al. 1981

J. Org. Chem.

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vco 1710; NMR 1.15 (s, 9 ), 1.3-2.4 (m, 8 ), 4.05 (br m, 1 H), 4.8 (br m, NH); 19F NMR 155.5 (not resolved m).4,5-Tetramethylene-2-oxazolidone ( 19): DR: yNH 3450 (sharp), 3250 (br), i/co 1750; NMR 1.3-2.2 (m, 8 H), 4 (t, J = 4,1 H), 6.45 (s, 1 H), 7.46 (s, 5 H).JV-(tert-Butoxycarbonyl)-l-ethyl-7-azabicyclo[4.1.0]heptane (20d): crude product, IR t>co 1710; NMR 0.8-1.9 (m exhibiting a sharp s at 1.4, 22 H), 2,3 (m, 1 H). A 1-g (4.4 mmol) sample of 20d was allowed to react with NR3-2.5HF. The crude solid isolated (970 mg) exhibited only one signal in the 19F NMR spectrum; its NMR spectrum was consistent with pure 21dT. The structure of 21dT was confirmed by its hydrolysis to the amine 21aT in Olah's reagent, followed by Schotten-Baumann benzoylation to 24bT.JV-(tert-Butoxycarbonyl)-2-fluoro-2-ethylcyclohexylamine (21dT): yield 90; mp 107-109 °C (CH3CN); IR -3440, vCo 1710; NMR 0.9 (2 overlapping t,J= 7), 1.4 (s) and 1.2-2,2 (m, total 22 H), 3,85 (br m, 1 H), 4,7 (br m, 1 H); mass spectrum, mje

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“…Lactones 17a and 45 were obtained from Aldrich and distilled before use. The following lactones are known compounds: 24, 36 27, 19 30, 37 33, 38 36, 39 39, 40 and 42. 41 Lactone 21 was prepared by the following procedure.…”

Section: Methodsmentioning

confidence: 99%

A Synthesis of α-Lithiated Enol Ethers from α-Arenesulfinyl Enol Ethers: Ni(0)- and Pd(0)-Catalysed Coupling of Enol Triflates and Phosphates Derived from Lactones with Sodium Arenethiolates Gives α-Arenesulfanyl Enol Ethers

Milne¹,

Kocieński²

2003

Synthesis

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A three-step synthesis of stable and storable α-benzenesulfinyl enol ethers from lactones entails (a) conversion of a lactone to an enol triflate or phosphate; (b) Ni(0) and Pd(0) cross-coupling of the enol triflate or phosphate with a sodium arenethiolate to give an α-arenethio enol ether; and (c) oxidation of an arenethio group to a sulfoxide. The α-benzenesulfinyl enol ethers undergo sulfoxidelithium exchange on reaction with n-BuLi to give α-lithiated enol ethers thus making the α-benzenesulfinyl group a surrogate for the trialkylstannyl group which has hitherto served as the most common precursor to α-lithiated enol ethers.

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Configuration and conformation of cis- and trans-3,5-dimethylvalerolactones

Cited by 38 publications

References 8 publications

Carbon-13 nuclear magnetic resonance spectroscopy of polycyclic .delta.-lactones

Carbon-13 nuclear magnetic resonance spectroscopy of polycyclic .delta.-lactones

Anomeric effect in 2-alkoxytetrahydropyrans studied by carbon-13 and oxygen-17 NMR chemical shifts

A Synthesis of α-Lithiated Enol Ethers from α-Arenesulfinyl Enol Ethers: Ni(0)- and Pd(0)-Catalysed Coupling of Enol Triflates and Phosphates Derived from Lactones with Sodium Arenethiolates Gives α-Arenesulfanyl Enol Ethers

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