ArticleChemical communications (Cambridge, England)2012
Chiral proton catalysis of secondary nitroalkane additions to azomethine: synthesis of a potent GlyT1 inhibitor.
Article in Chemical communications (Cambridge, England), 2012. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 18 papers.
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Who cites it
18 citing papers in PubMed, 51 citations in OpenAlex.
- Generality-Driven Catalyst Development: A Universal Catalyst for Enantioselective Nitroalkene Reduction.Journal of the American Chemical Society · 2024Article
- DFT-Based Stereochemical Rationales for the Bifunctional Brønsted Acid/Base-Catalyzed Diastereodivergent and Enantioselective aza-Henry Reactions of α-Nitro Esters.The Journal of organic chemistry · 2021Article
- Synthesis of Boronated Amidines by Addition of Amines to Nitrilium Derivative of Cobalt Bis(Dicarbollide).Molecules (Basel, Switzerland) · 2021Article
- New α-Hydrazinophosphonic acid: Synthesis, characterization, DFT study and in silico prediction of its potential inhibition of SARS-CoV-2 main protease.Journal of molecular structure · 2021Article
- The Stereoselective Nitro-Mannich Reaction in the Synthesis of Active Pharmaceutical Ingredients and Other Biologically Active Compounds.Frontiers in chemistry · 2020Review
- The inverted ketene synthon: a double umpolung approach to enantioselective βChemical science · 2019Article
- Catalytic, Enantioselective Synthesis of Cyclic Carbamates from Dialkyl Amines by COJournal of the American Chemical Society · 2019Article
- Continuous Platform to Generate Nitroalkanes On-Demand (in situ) using Peracetic Acid-Mediated Oxidation in a PFA Pipes-in-Series Reactor.Organic process research & development · 2018Article
- Diastereo- and enantioselective additions of α-nitro esters to imines forChemical science · 2018Article
- One-pot multicomponent nitro-Mannich reaction using a heterogeneous catalyst under solvent-free conditions.PeerJ · 2018Article
- Development of an Intermittent-Flow Enantioselective Aza-Henry Reaction Using an Arylnitromethane and Homogeneous Brønsted Acid-Base Catalyst with Recycle.Organic process research & development · 2016Article
- Adaptation of a small-molecule hydrogen-bond donor catalyst to an enantioselective hetero-Diels-Alder reaction hypothesized for brevianamide biosynthesis.Organic letters · 2015Article
- Organocatalytic, diastereo- and enantioselective synthesis of nonsymmetric cis-stilbene diamines: a platform for the preparation of single-enantiomer cis-imidazolines for protein-protein inhibition.The Journal of organic chemistry · 2014Article
- Novel GlyT1 inhibitor chemotypes by scaffold hopping. Part 2: development of a [3.3.0]-based series and other piperidine bioisosteres.Bioorganic & medicinal chemistry letters · 2014Article
- Preparation of (-)-Nutlin-3 using enantioselective organocatalysis at decagram scale.The Journal of organic chemistry · 2013Article
- Synthesis of the reported structure of piperazirum using a nitro-Mannich reaction as the key stereochemical determining step.Beilstein journal of organic chemistry · 2013Article
- Organocatalytic, enantioselective synthesis of VNI: a robust therapeutic development platform for Chagas, a neglected tropical disease.Organic letters · 2012Article
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Authors and funding
3 authors at 1 institution in 1 country.
Funding
Abstract
The first enantioselective synthesis of a potent GlyT1 inhibitor is described. A 3-nitroazetidine donor is used in an enantioselective aza-Henry reaction catalyzed by a bis(amidine)-triflic acid salt organocatalyst, delivering the key intermediate with 92% ee. This adduct is reductively denitrated and converted to the target through a short sequence, thereby allowing assignment of the absolute configuration of the more potent enantiomer.
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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.