Organic Letters 2003-12-11

Stereoselective ring opening of meso bicyclic hydrazines: a straightforward approach to hydrazino cyclopentenic cores.

Alejandro Pérez Luna, Michèle Cesario, Martine Bonin, Laurent Micouin

Index: Org. Lett. 5 , 4771, (2003)

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Abstract

The diastereoselective synthesis of hydrazinocyclopentenes 6 or 7 can be achieved in a straightforward manner from Diels-Alder adduct 4 using an acid-catalyzed rearrangement or a palladium-catalyzed allylic substitution reaction. In the latter case, enantioenriched compounds with ee values up to 58% can be obtained when an appropriate chiral ligand is used. [reaction: see text]