Academic Journal

Bicyclic allyltin derivatives through selective "one pot" hydrostannation - Diels-Alder reaction.

التفاصيل البيبلوغرافية
العنوان: Bicyclic allyltin derivatives through selective "one pot" hydrostannation - Diels-Alder reaction.
المؤلفون: Ocampo, Romina A.1, Mandolesi, Sandra D.1, Koll, Liliana C.1 lckoll@criba.edu.ar
المصدر: ARKIVOC: Online Journal of Organic Chemistry. 2011, p195-209. 15p.
مصطلحات موضوعية: *BICYCLIC compounds, *DIELS-Alder reaction, *CHEMICAL derivatives, *RADICALS (Chemistry), *RING formation (Chemistry), *SUBSTITUENTS (Chemistry)
مستخلص: In this paper we report a simple "one pot" procedure to functionalized allyltin derivatives from 1- ethynylcyclohexene. Radical addition of trineophyltin hydride gives quantitatively to (Z,E)-1-(2- trineophylstannylvinyl)cyclohexene, a conjugated dienyl-stannane that, via a [4+2] cycloaddition reaction (Diels-Alder) with activated dienophiles, affords substituted bicyclic unsaturated products with specific stereochemistry and a trialkylstannyl group in allylic position. The Stille reaction of the allyltin compound enables the synthesis of aryl substituted bicyclic compounds in moderate to good yields (48-85%). [ABSTRACT FROM AUTHOR]
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