✍ Scribed by Liu-Zhu Gong; Lin Pu
No coin nor oath required. For personal study only.
By varying the substituents on the nitrogen of enamide aldehydes, their reaction mode with Danishefsky's diene in the presence of Lewis acid catalysts can be controlled and the desired formal hetero-Diels-Alder products obtained. A new and efficient method to synthesize chiral binaphthyl ligands containing sterically bulky 3,3substituents has been developed. Lewis acid complexes prepared from these binaphthyl ligands and AlMe 3 are used to catalyze the hetero-Diels-Alder reaction of an enamide aldehyde with Danishefsky's diene with up to 78% ee. This catalytic asymmetric reaction may allow for the efficient synthesis of biologically interesting molecules such as fumonisins.
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