Tandem Prins/Friedel-Crafts cyclization for stereoselective synthesis of heterotricyclic systems. - Université de Rennes Accéder directement au contenu
Article Dans Une Revue Journal of Organic Chemistry Année : 2011

Tandem Prins/Friedel-Crafts cyclization for stereoselective synthesis of heterotricyclic systems.

Basi V. Subba Reddy
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Prashant Borkar
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Jhillu Singh Yadav
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B. Sridhar
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René Grée
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Résumé

Homoallylic substrates such as (E)-6-arylhex-3-enyl alcohols, N-tosylamides, and thiols undergo smooth cross-coupling with various aldehydes in the presence of 10 mol % Sc(OTf)3 and 30 mol % TsOH to afford the trans-fused hexahydro-1H-benzo[f]isochromenes, N-tosyloctahydrobenzo[f]isoquinolines, and hexahydro-1H-benzo[f]isothiochromenes, respectively. However, the cross-coupling of (Z)-olefins such as 6-arylhex-3-enyl alcohols, N-tosylamides, and thiols with aldehydes affords the corresponding hexahydro-1H-benzo[f]isochromenes, N-tosyloctahydrobenzo[f]isoquinolines, and hexahydro-1H-benzo[f]isothiochromenes with complete cis selectivity via intramolecular Prins-, aza-Prins-, and thia-Prins/Friedel-Crafts cyclizations, respectively. Though the Prins cyclization proceeds smoothly under the influence of Sc(OTf)3, high conversions and enhanced reaction rates are achieved using a mixture of Sc(OTf)3 and TsOH (1:3).

Domaines

Chimie organique
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Dates et versions

hal-00843842 , version 1 (12-07-2013)

Identifiants

Citer

Basi V. Subba Reddy, Prashant Borkar, Jhillu Singh Yadav, B. Sridhar, René Grée. Tandem Prins/Friedel-Crafts cyclization for stereoselective synthesis of heterotricyclic systems.. Journal of Organic Chemistry, 2011, 76 (19), pp.7677-90. ⟨10.1021/jo201027u⟩. ⟨hal-00843842⟩
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