2023
DOI: 10.1002/anie.202303670
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Construction of Axially Chiral Arylpyrroles via Atroposelective Diyne Cyclization

Abstract: Axially chiral biaryls widely exist in natural products and pharmaceuticals and are used as chiral ligands and catalysts in asymmetric synthesis. Compared to the well-established axially chiral 6-membered biaryl skeletons, examples of 5-membered biaryls have been quite scarce, and mono-substituted 3-arylpyrrole atropisomers have not been reported. Here, we disclose a copper-catalyzed atroposelective diyne cyclization for the construction of a range of axially chiral arylpyrrole biaryls in good to excellent yie… Show more

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Cited by 34 publications
(10 citation statements)
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“…Plausible reaction mechanism. On the basis of the above experimental results and our previous study on the copper-catalyzed cyclization of N-propargyl ynamides [38][39][40][41][42][43][44][45][46][47] , a plausible reaction mechanism to rationalize the formation of pyrrole-substituted oxadiazine 3a is shown in Fig. 6.…”
Section: Resultsmentioning
confidence: 70%
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“…Plausible reaction mechanism. On the basis of the above experimental results and our previous study on the copper-catalyzed cyclization of N-propargyl ynamides [38][39][40][41][42][43][44][45][46][47] , a plausible reaction mechanism to rationalize the formation of pyrrole-substituted oxadiazine 3a is shown in Fig. 6.…”
Section: Resultsmentioning
confidence: 70%
“…Screening of reaction conditions. To prohibit the background C-H insertion reaction 38 , 2,6-dimethylphenyl-substituted Npropargyl ynamide 1a was first chosen as the model substrate to react with 1,2,5-oxadiazole 2a under our previous related reaction conditions [38][39][40][41][42][43][44][45][46][47] , and selected results are listed in Table 1. To our delight, the expected 1,2,5-oxadiazine 3a was indeed formed in 37% yield in the presence of 10 mol % of CuOTf as catalyst (Table 1, entry 1).…”
Section: Resultsmentioning
confidence: 99%
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“…However, most of them allow access to only pyrrole-derived atropisomers with a C–N 6 rotational axis. The preparation of pyrroles with N–N 7 or C–C 8 bonds has been much less studied ( Scheme 1 ). In fact, to the best of our knowledge, only three procedures describe the enantioselective preparation of axially chiral C2-arylpyrroles.…”
mentioning
confidence: 99%