Memory of Chirality in Cascade Rearrangements of Enediynes

Malek Nechab (1) , Damien Campolo (1) , Julien Maury (2) , Patricia Perfetti , Nicolas Vanthuyne (3) , Didier Siri (1) , Michèle P. Bertrand (1)

1 ICR - Institut de Chimie Radicalaire
2 IBMM - Institut des Biomolécules Max Mousseron [Pôle Chimie Balard]
3 ChiroSciences

The cascade rearrangement of chiral enediynes 1c-e, involving successively 1,3-proton shift, Saito-Myers cyclization, 1,5-hydrogen atom transfer, and intramolecular coupling of the resulting biradical, proceeded at 80 degrees C to form tri- and tetracyclic heterocycles possessing a quaternary stereogenic center with a very high level of memory of chirality.

Domaines: Chimie

Malek Nechab, Damien Campolo, Julien Maury, Patricia Perfetti, Nicolas Vanthuyne, et al.. Memory of Chirality in Cascade Rearrangements of Enediynes. Journal of the American Chemical Society, 2010, 132 (42), pp.14742--14744. ⟨10.1021/ja106668d⟩. ⟨hal-01460245⟩