Asymmetric Diels−Alder Reactions of a New Enantiomerically Pure
Sulfinylquinone: A Straightforward Access to Functionalized
Wieland−Miescher Ketone Analogues with (R) Absolute
Configuration
posted on 2006-06-23, 00:00authored byDon Antoine Lanfranchi, Gilles Hanquet
An efficient and highly stereocontrolled preparation, on a large scale, of two new Wieland−Miescher-type diketones is described. The approach centers on a diastereoselective Diels−Alder reaction using a
new enantiomerically pure sulfinylquinone. Mechanistic investigations of this cycloaddition on several
dienes are described.