An Easy, Stereoselective Synthesis of Hexahydroisoindol-4-ones under Phosphine Catalysis

Abstract : A new synthetic approach to hexahydroisoindol-4-ones is reported, based on the formal [3+2] cyclization reaction between N-arylsulfonylimines and cyclic conjugated dienes, under phosphine catalysis. Key substrates are 3-vinylcyclohex-2-enones with electron-withdrawing substituents (ester, amido, cyano, phosphoryl and keto groups) on the exocyclic double bond, which afford the three atom synthons for the construction of the pyrroline ring. Total syn stereoselectivity is observed in these annulations. The scope of the reaction has been demonstrated and mechanistic issues are considered, based on deuteration experiments and DFT calculations.
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Soumis le : jeudi 3 mars 2011 - 16:21:19
Dernière modification le : mardi 11 juin 2019 - 12:02:05
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Deepti Duvvuru, Jean-François Betzer, Pascal Retailleau, Gilles Frison, Angela Marinetti. An Easy, Stereoselective Synthesis of Hexahydroisoindol-4-ones under Phosphine Catalysis. Advanced Synthesis and Catalysis, Wiley-VCH Verlag, 2011, 353, pp.483-493. ⟨10.1002/adsc.201000701⟩. ⟨hal-00554156⟩



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