New, Facile Synthesis of 3,3-Disubstituted Phthalides Based on the Reaction of α-Substituted 2-Lithiostyrenes with Carbon Dioxide

Kobayashi, Kazuhiro; Kozuki, Taketoshi; Fukamachi, Shuhei; Konishi, Hisatoshi

doi:10.3987/com-09-11837

Cited by 10 publications

(2 citation statements)

References 32 publications

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“…Substrates having a thienyl group also furnished the desired product 5g but in moderate yield due to the formation of the HOAc-promoted lactonization product 5g′. 10 Satisfactorily, substrates containing a chloro or bromo group in the 4-or 5-position of the benzoic acid unit also produced the desired lactones in good yields (5h-5k). Furthermore, carboxylic acid with an internal alkene (R 5 = Me) also underwent cyclization to give the lactone 5l in 64% yield.…”

Section: Resultsmentioning

confidence: 99%

Transition-metal free thiocyanooxygenation of functionalized alkenes: facile routes to SCN-containing dihydrofurans and lactones

Guo

et al. 2016

Org. Biomol. Chem.

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An efficient transition-metal free tandem cyclization of functionalized alkenes with easily available thiocyanate salts has been developed under mild conditions. This protocol offers a simple, easy-to-handle, and atom-economical method for the synthesis of SCN-containing dihydrofurans and lactones with good to excellent yields. A detailed mechanistic investigation indicates that a tandem radical pathway is involved in this transformation.

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Section: Resultsmentioning

confidence: 99%

Transition-metal free thiocyanooxygenation of functionalized alkenes: facile routes to SCN-containing dihydrofurans and lactones

Guo

et al. 2016

Org. Biomol. Chem.

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“…The synthesis of 3,3-disubstituted phthalides from 2-bromostyrenes 307 was developed on the basis of metal–halogen exchange . The lithio-derivatives 308 , derived from 307 , on reaction with carbon dioxide gave the corresponding lithium 2-vinylbenzoates 309 , which on acidolysis afforded phthalides 310 via protolactonization (Scheme ).…”

Section: Phthalidesmentioning

confidence: 99%

Phthalides and Phthalans: Synthetic Methodologies and Their Applications in the Total Synthesis

2014

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Scheme 10. Schmalz Synthesis of 3-Substituted Phthalides from 2-Formylketones Scheme 11. Enantioselective Synthesis of Phthalides via Ketone Hydroacylation Scheme 12. Synthesis of 3-Alkylphthalides from Sulfonylmethyl Benzoic Acids Scheme 13. Synthesis of an Isobenzofuranone via Thermolysis of a Bromomethylbenzoate Scheme 14. Kraus Approach to 3-Cyanophthalide Scheme 15. Ohzeki and Mori Synthesis of (−)-3-Butyl-7hydroxyphthalide Scheme 16. Asymmetric Dihydroxylation-Lactonization Route to Phthalides Chemical Reviews Review dx.

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Ene‐Carbonyl Reductive Coupling for the Synthesis of 3,3‐Disubstituted Phthalide, 3‐Hydroxyisoindolin‐1‐one and 3‐Hydroxyoxindole Derivatives

et al. 2014

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An efficient method for the synthesis of three classes of heterocyclic derivatives such as 3,3disubstituted phthalides, 3-hydroxyisoindolin-1-ones and 3-hydroxyoxindoles, is reported. In the presence of the simple reductive system, zinc (Zn)/ammonia (NH 3 ) [or zinc-copper (Zn-Cu)/ammonia], a wide range of alkenes including acrylates, acrylonitrile, acrylamide and vinyl sulfoxide underwent reductive coupling with methyl 2-acylbenzoates and subsequent lactonization to provide 3,3-disubstituted phthalides in good to high yields at ambient temperature. In a similar manner, 3-hydroxyisoindolin-1one and 3-hydroxyoxindole derivatives could also be easily prepared by direct reductive coupling of phthalimides and N-substituted isatins with activated alkenes, respectively. Application of this methodology towards the synthesis of 1-naphthol derivatives on a gram scale is also depicted. Furthermore, the intramolecular phthalimides-ene reductive coupling afforded the respective cyclization products with high diastereoselectivity.Scheme 1. Optimization studies for the reductive coupling of methyl 2-benzoylbenzoate (1a) with acrylamide (2e).Scheme 2. Reductive couplings of 1l with 2b, 1m with 2c and 1a with 4. Scheme 4. Dieckmann condensation to afford a 1-naphthol derivative.Scheme 5. Oxidative removal of the N-a-methyl-4-methoxybenzyl group. 838

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New, Facile Synthesis of 3,3-Disubstituted Phthalides Based on the Reaction of α-Substituted 2-Lithiostyrenes with Carbon Dioxide

Cited by 10 publications

References 32 publications

Transition-metal free thiocyanooxygenation of functionalized alkenes: facile routes to SCN-containing dihydrofurans and lactones

Transition-metal free thiocyanooxygenation of functionalized alkenes: facile routes to SCN-containing dihydrofurans and lactones

Phthalides and Phthalans: Synthetic Methodologies and Their Applications in the Total Synthesis

Ene‐Carbonyl Reductive Coupling for the Synthesis of 3,3‐Disubstituted Phthalide, 3‐Hydroxyisoindolin‐1‐one and 3‐Hydroxyoxindole Derivatives

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