Stereoselective Synthesis of cis-1,3-Dimethyltetrahydroisoquinolines: Formal Synthesis of Naphthylisoquinoline Alkaloids

[摘要]：A synthetic route to enantiopure cis-1,3-dimethyltetrahydroisoquinolines, synthetic precursors of naphthylisoquinoline alkaloids, has been developed. The synthesis relies on the use of a phenylglycinol-derived lactam as the starting enantiopure scaffold. After stereoselective opening of the oxazolidine ring, the C-3 methyl substituent was installed, taking advantage of the lactam carbonyl group by stereoselective hydrogenation of an a-methylenamide generated via a vinyl triflate.

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