ArticleOrganic letters2014
Stereocontrolled synthesis of bicyclic sulfamides via Pd-catalyzed alkene carboamination reactions. Control of 1,3-asymmetric induction by manipulating mechanistic pathways.
Article in Organic letters, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
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Who cites it
8 citing papers in PubMed.
- Pd/Xiang-Phos-catalyzed enantioselective intermolecular carboheterofunctionalization under mild conditions.Chemical science · 2020Article
- Pd-Catalyzed C-C, C-N, and C-O Bond-Forming Difunctionalization Reactions of Alkenes Bearing Tethered Aryl/Alkenyl Triflates.Israel journal of chemistry · 2020Article
- Stereocontrolled synthesis of bicyclic ureas and sulfamides via Pd-catalyzed alkene carboamination reactions.Tetrahedron · 2019Article
- Synthesis of Cyclic Guanidines Bearing N-Arylsulfonyl and N-Cyano Protecting Groups via Pd-Catalyzed Alkene Carboamination Reactions.Organic letters · 2017Article
- Recent Developments in Pd(0)-Catalyzed Alkene Carboheterofunctionalization Reactions.Asian journal of organic chemistry · 2017Article
- Synthesis of 2,3-Dihydrobenzofurans via the Palladium Catalyzed Carboalkoxylation of 2-Allylphenols.Organic chemistry frontiers : an international journal of organic chemistry · 2016Article
- Asymmetric Palladium-Catalyzed Alkene Carboamination Reactions for the Synthesis of Cyclic Sulfamides.Chemistry (Weinheim an der Bergstrasse, Germany) · 2016Article
- Synthesis of substituted 2-aminoimidazoles via Pd-catalyzed alkyne carboamination reactions. Application to the synthesis of preclathridine natural products.Organic letters · 2014Article
Corrections and comments
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Authors and funding
4 authors.
Funding
Abstract
A new annulation strategy for the synthesis of trans-bicyclic sulfamides is described. The Pd-catalyzed alkene carboamination reactions of 2-allyl and cis-2,5-diallyl pyrrolidinyl sulfamides with aryl and alkenyl triflates afford the fused bicyclic compounds in good yields and with good diastereoselectivity (up to 13:1 dr). Importantly, by employing reaction conditions that favor an anti-aminopalladation mechanism, the relative stereochemistry between the C3 and C4a stereocenters of the products is reversed relative to related Pd-catalyzed carboamination reactions that proceed via syn-aminopalladation.
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Registered trials
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