ArticleACS catalysis2018
Enantioselective Organocatalytic Amine-Isocyanate Capture-Cyclization: Regioselective Alkene Iodoamination for the Synthesis of Chiral Cyclic Ureas.
Article in ACS catalysis, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 4 papers.
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Who cites it
4 citing papers in PubMed, 36 citations in OpenAlex.
- Progress in Stereoselective Haloamination of Olefins.Molecules (Basel, Switzerland) · 2025Review
- Photo- and Cobalt-Catalyzed Cycloisomerization of Unsaturated Guanidines, (Iso-)Ureas, and Carbonates.Organic letters · 2025Article
- Enantioselective iodolactonization to prepare ε-lactone rings using hypervalent iodine.Chemical science · 2022Article
- Ritter-enabled catalytic asymmetric chloroamidation of olefins.Chemical science · 2020Article
Corrections and comments
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Authors and funding
4 authors at 2 institutions in 1 country.
Funding
Abstract
Ureas of chiral diamines are prominent features of therapeutics, chiral auxiliaries, and intermediates in complex molecule synthesis. Although many methods for diamine synthesis are available, metal-free enantioselective alkene functionalizations to make protected 1,2- and 1,3-diamines from simple achiral starting materials are rare, and a single reagent that accesses a cross-section of each congener with high enantiomeric excess is not available. We describe a method to synthesize enantioenriched cyclic 5- and 6-membered ureas from allylic amines and an isocyanate using a C2-symmetric BisAmidine (BAM) catalyst that delivers N-selectivity from an ambident sulfonyl imide intermediate, overcoming electronic and steric deactivation at nitrogen. The geometry of 1,2-disubstituted alkenes is correlated to 5-exo and 6-endo cyclizations without altering alkene face selectivity, which is unexpectedly opposite that observed with O-nucleophiles. Straightforward product manipulations to diamine and imidazolidinone derivatives are underscored by the synthesis of an NK1 antagonist.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.