An efficient one-pot approach to bridged bicyclic ring-systems through consecutive hetero-domino transformations: a mechanistic rationale and further rearrangements.
This article describes the design of olefin-generated/reagent-modulated consecutive hetero-domino reactions of 1,2-unsaturated bicyclic diols, which are potentially of great use, initiated by PhI(OAc)(2), continued by [Pb(OAc)(4)], and completed by use of a mild base (K(2)CO(3)). Inversion of a quaternary center has been achieved through a three-reaction sequence: a domino transformation followed by an m-CPBA-mediated Baeyer-Villiger oxidation and subsequent reductive lactone ring opening.
Finet
Laure
L
Institut de Chimie des Substances Naturelles, CNRS Avenue de la Terrasse 91198 Gif-sur Yvette, France.
Candela Lena
José I
JI
Kaoudi
Talbi
T
Birlirakis
Nicolas
N
Arseniyadis
Siméon
S