Chiral Dienophiles Derived from Malic Acid: Synthesis of (Z)-(2S)-(tert-Butyl)-5-(ethoxycarbonylmethylene)-1,3-dioxolan-4-one and Its Diels-Alder Reaction with Cyclopentadiene
17 September 2002 (online)
The synthesis of title chiral olefin 12 is described. Its structure is determined by X-ray analysis. The Diels-Alder reaction of 12 with cyclopentadiene exclusively yields the exo products with a face selectivity up to 95%.