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Issue 8, 2003
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Synthesis of spirocycles via ring closing metathesis of heterocycles carrying gem-diallyl substituents obtained via ring opening of (halomethyl)cyclopropanes with allyltributyltin

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Abstract

In the presence of allyl tri-n-butyltin–AIBN, cyclopropylmethyl bromides/xanthates undergo ring-opening reaction with concomitant formation of geminal diallyl derivatives in good yields. The ring closing metathesis reactions on geminal diallyl derivatives with Grubbs' catalyst provided spirocyclopentenyl products. Combination of these two methodologies has been applied to the synthesis of mono-, bis-cyclopentyl-carbohydrates as well as spirocyclopentylproline derivatives.

Graphical abstract: Synthesis of spirocycles via ring closing metathesis of heterocycles carrying gem-diallyl substituents obtained via ring opening of (halomethyl)cyclopropanes with allyltributyltin

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Publication details

The article was received on 09 Jan 2003, accepted on 10 Feb 2003 and first published on 20 Mar 2003


Article type: Paper
DOI: 10.1039/B300314K
Citation: Org. Biomol. Chem., 2003,1, 1366-1373
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    Synthesis of spirocycles via ring closing metathesis of heterocycles carrying gem-diallyl substituents obtained via ring opening of (halomethyl)cyclopropanes with allyltributyltin

    M. K. Gurjar, S. V. Ravindranadh, K. Sankar, S. Karmakar, J. Cherian and M. S. Chorghade, Org. Biomol. Chem., 2003, 1, 1366
    DOI: 10.1039/B300314K

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