Friedel-Crafts Reaction Involving Unsaturated Ketones and Esters. II. Convenient Syntheses of some Alkylnaphthalenes

Muhkerji, S. M.; Vig, O. P.; Singh, Satnam; Bhattacharyya, N. K.

doi:10.1021/jo50017a007

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Cited by 5 publications

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“…Literature precedent indicated that more success might be achieved with organomagnesium reagents . Thus a Li−Mg-exchange reaction was effected by treating the organolithium with solid anhydrous MgBr 2 .…”

Section: Resultsmentioning

confidence: 99%

Development of a Protocol for Eight- and Nine-Membered Ring Synthesis in the Annulation of sp²,sp³-Hybridized Organic Dihalides with Keto Esters

Molander

Köllner

2000

J. Org. Chem.

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A protocol has been developed in which annulation reactions of various dihalides with keto esters can be carried out to provide entry to eight- and nine-membered carbocycles. In this process wherein one alkenyl- or aryl bromide and a tethered alkyl chloride comprise the organic dihalide, a selective metal-halogen exchange reaction between the sp(2)-hybridized bromide and an organolithium initiates the process. Transmetalation to an organoytterbium reagent generates a species that undergoes selective carbonyl addition to the ketone of the keto ester, creating a lactone intermediate. Subjection of the resulting chloroalkyl lactone to intramolecular reductive coupling with samarium(II) iodide completes the desired annulation.

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Section: Resultsmentioning

confidence: 99%

Development of a Protocol for Eight- and Nine-Membered Ring Synthesis in the Annulation of sp²,sp³-Hybridized Organic Dihalides with Keto Esters

Molander

Köllner

2000

J. Org. Chem.

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Preparation of Esters

1971

Compendium of Organic Synthetic Methods

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Studies in sesquiterpenes—XLI

Prahlad

Dev

1970

Tetrahedron

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Friedel-Crafts Reaction Involving Unsaturated Ketones and Esters. II. Convenient Syntheses of some Alkylnaphthalenes

Cited by 5 publications

References 9 publications

Development of a Protocol for Eight- and Nine-Membered Ring Synthesis in the Annulation of sp²,sp³-Hybridized Organic Dihalides with Keto Esters

Development of a Protocol for Eight- and Nine-Membered Ring Synthesis in the Annulation of sp²,sp³-Hybridized Organic Dihalides with Keto Esters

Preparation of Esters

Studies in sesquiterpenes—XLI

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Friedel-Crafts Reaction Involving Unsaturated Ketones and Esters. II. Convenient Syntheses of some Alkylnaphthalenes

Cited by 5 publications

References 9 publications

Development of a Protocol for Eight- and Nine-Membered Ring Synthesis in the Annulation of sp2,sp3-Hybridized Organic Dihalides with Keto Esters

Development of a Protocol for Eight- and Nine-Membered Ring Synthesis in the Annulation of sp2,sp3-Hybridized Organic Dihalides with Keto Esters

Preparation of Esters

Studies in sesquiterpenes—XLI

Contact Info

Product

Resources

About

Development of a Protocol for Eight- and Nine-Membered Ring Synthesis in the Annulation of sp²,sp³-Hybridized Organic Dihalides with Keto Esters

Development of a Protocol for Eight- and Nine-Membered Ring Synthesis in the Annulation of sp²,sp³-Hybridized Organic Dihalides with Keto Esters