Sequential Organocatalyzed Michael Addition/[3 + 2]-Heterocyclization for the Stereoselective Synthesis of Fused-Isoxazoline Precursors of Enantiopure Cyclopentanoids - Archive ouverte HAL Access content directly
Journal Articles Organic Letters Year : 2008

Sequential Organocatalyzed Michael Addition/[3 + 2]-Heterocyclization for the Stereoselective Synthesis of Fused-Isoxazoline Precursors of Enantiopure Cyclopentanoids

Damien Bonne
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Lydie Salat
  • Function : Author
Jean-Pierre Dulcère
  • Function : Author
Jean Rodriguez
  • Function : Correspondent author
  • PersonId : 921781
  • IdRef : 260692638

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Abstract

We propose an asymmetric synthesis of functionalized cyclopentanoids bearing up to four stereogenic centers from easily accessible nitroalkenes and unsaturated aldehydes. The overall sequence includes an enantioselective organocatalytic Michael addition and a [3 + 2]-heterocyclization between an in situ generated silylnitronate and the unactivated double bond. Finally, the fused isoxazoline can be further transformed to various cyclopentanoids.
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hal-00677496 , version 1 (08-03-2012)

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Damien Bonne, Lydie Salat, Jean-Pierre Dulcère, Jean Rodriguez. Sequential Organocatalyzed Michael Addition/[3 + 2]-Heterocyclization for the Stereoselective Synthesis of Fused-Isoxazoline Precursors of Enantiopure Cyclopentanoids. Organic Letters, 2008, 10, pp.5409-5412. ⟨10.1021/ol8023133⟩. ⟨hal-00677496⟩
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