期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 85, 期 16, 页码 10797-10805出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.0c01311
关键词
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An asymmetric synthesis of the tetrahydronaphthyridine scaffold of TAIL-828F as a ROR gamma t inverse agonist has been developed. The synthesis features a newly discovered atom-economical protocol for Heck-type vinylation of chloropyridine using ethylene gas, an unprecedented formation of dihydronaphthyridine directly from 2-vinyl-3-acylpyridine mediated by ammonia, and a ruthenium-catalyzed enantioselective transfer hydrogenation as key steps. This represents the first example of the enantioselective synthesis of a 5,6,7,8-tetrahydro-1,6-naphthyridine compound. The new synthesis is also free of chromatography or distillation purification processes and therefore qualifies for extension to large-scale manufacture.
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