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- W4224279103 abstract "Tropane derivatives are extensively used in medicine, but catalytic asymmetric methods for their synthesis are underexplored. Here we report Rh-catalysed asymmetric Suzuki-Miyaura type crosscoupling reactions between a racemic N-Boc-nortropane-derived allylic chloride and (hetero-)aryl-boronic esters. The reaction proceeds via an unexpected kinetic resolution, and the resolved enantiopure allyl chloride can undergo highly enantiospecific reactions with N, O, and S-containing nucleophiles. The method was applied in a highly stereoselective formal synthesis of YZJ-1139(1), a potential insomnia treatment that recently completed Phase II clinical trials. Our report represents the first synthesis of YZJ-1139(1) and related compounds using asymmetric catalysis." @default.
- W4224279103 created "2022-04-26" @default.
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- W4224279103 date "2022-04-19" @default.
- W4224279103 modified "2023-10-16" @default.
- W4224279103 title "Asymmetric synthesis of nortropanes via Rh-catalysed allylic arylation" @default.
- W4224279103 doi "https://doi.org/10.26434/chemrxiv-2022-qfp1d" @default.
- W4224279103 hasPublicationYear "2022" @default.
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