Asymmetric Synthesis of Nortropanes via Rh-Catalyzed Allylic Arylation.

Content Provider	Europe PMC
Author	Zhang, Yan Goetzke, F. Wieland Christensen, Kirsten E. Fletcher, Stephen P.
Copyright Year	2022
Abstract	Tropane derivatives are extensively used in medicine,but catalyticasymmetric methods for their synthesis are underexplored. Here, wereport Rh-catalyzed asymmetric Suzuki–Miyaura-type cross-couplingreactions between a racemic N-Boc-nortropane-derivedallylic chloride and (hetero)aryl boronic esters. The reaction proceeds via an unexpected kinetic resolution, and the resolved enantiopureallyl chloride can undergo highly enantiospecific reactions with N-,O-, and S-containing nucleophiles. The method was applied in a highlystereoselective formal synthesis of YZJ-1139(1), a potential insomniatreatment that recently completed Phase II clinical trials. Our reportrepresents an asymmetric catalytic method for the synthesis of YZJ-1139(1)and related compounds.
Related Links	https://europepmc.org/backend/ptpmcrender.fcgi?accid=PMC9361292&blobtype=pdf
Journal	ACS Catalysis [ACS Catal]
Volume Number	12
DOI	10.1021/acscatal.2c02259
PubMed Central reference number	PMC9361292
Issue Number	15
PubMed reference number	35966601
e-ISSN	21555435
Language	English
Publisher	American Chemical Society
Publisher Date	2022-07-12
Access Restriction	Open
Rights License	Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/). © 2022 The Authors. Published by American Chemical Society
Subject Keyword	alkaloids asymmetric catalysis bicycles rhodium Suzuki−Miyaura coupling kineticresolution
Content Type	Text
Resource Type	Article
Subject	Chemistry Catalysis