ArticleJournal of the American Chemical Society2013
Squaramide-catalyzed enantioselective Michael addition of masked acyl cyanides to substituted enones.
Article in Journal of the American Chemical Society, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 21 papers.
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Who cites it
21 citing papers in PubMed.
- Bifunctional Monothiosquaramide-Catalyzed Enantioselective Addition of Masked Acyl Cyanide to Isatins: Umpolung Strategy for the Total Synthesis of (Organic letters · 2026Article
- Rapid Synthesis of anti-1,3-Diamino-4-phenylbutan-2-ol Building Blocks via a Three-Component Oxyhomologation and a Two-Component Reducing System.ChemistryOpen · 2025Article
- Squaramide-catalyzed enantioselective Michael addition of nitromethane to 2-enoylazaarenes: synthesis of chiral azaarene-containing γ-nitroketones.RSC advances · 2024Article
- Catalytic Asymmetric Difluoroalkylation Using In Situ Generated Difluoroenol Species as the Privileged Synthon.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024Article
- Scalable Preparation of the Masked Acyl Cyanide TBS-MAC.Molecules (Basel, Switzerland) · 2023Article
- Enantioselective direct Michael addition of cyanohydrin ether derivatives to enones catalyzed by chiral bis(guanidino)iminophosphorane organosuperbase.Chemical science · 2023Article
- Catalytic aza-Nazarov cyclization reactions to access α-methylene-γ-lactam heterocycles.Beilstein journal of organic chemistry · 2023Article
- Bifunctional Iminophosphorane-Catalyzed Enantioselective Sulfa-Michael Addition to Unactivated α,β-Unsaturated Amides.Journal of the American Chemical Society · 2022Article
- A bifunctional iminophosphorane squaramide catalyzed enantioselective synthesis of hydroquinazolinesChemical science · 2021Article
- Intermolecular Stereoselective Iridium-Catalyzed Allylic Alkylation: An Evolutionary Account.Synlett : accounts and rapid communications in synthetic organic chemistry · 2018Article
- Controlling, Understanding, and Redirecting the Thermal Rearrangement of 3,3-Dicyano-1,5-enynes.Journal of the American Chemical Society · 2018Article
- Synthesis of 1,2-Oxazinanes via Hydrogen Bond Mediated [3 + 3] Cycloaddition Reactions of Oxyallyl Cations with Nitrones.Organic letters · 2018Article
- Macrolide and phenolic metabolites from the marine-derived fungus Paraconiothyrium sp. VK-13 with anti-inflammatory activity.The Journal of antibiotics · 2018Article
- A complementary pair of enantioselective switchable organocatalysts.Chemical science · 2017Article
- Enantioselective Synthesis of Acyclic α-Quaternary Carboxylic Acid Derivatives through Iridium-Catalyzed Allylic Alkylation.Angewandte Chemie (International ed. in English) · 2017Article
- Enantioselective Iridium-Catalyzed Allylic Alkylation Reactions of Masked Acyl Cyanide Equivalents.Organic letters · 2017Article
- Sterically Demanding Oxidative Amidation of α-Substituted Malononitriles with Amines Using O2.Angewandte Chemie (International ed. in English) · 2016Article
- Total Syntheses and Biological Evaluation of Both Enantiomers of Several Hydroxylated Dimeric Nuphar Alkaloids.Angewandte Chemie (International ed. in English) · 2015Article
- Organocatalytic and enantioselective Michael reaction between α-nitroesters and nitroalkenes. Syn/anti-selectivity control using catalysts with the same absolute backbone chirality.Beilstein journal of organic chemistry · 2015Article
- Enantioselective selenocyclization via dynamic kinetic resolution of seleniranium ions by hydrogen-bond donor catalysts.Journal of the American Chemical Society · 2014Article
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Authors and funding
4 authors.
Funding
Abstract
Masked acyl cyanide (MAC) reagents are shown to be effective umpolung synthons for enantioselective Michael addition to substituted enones. The reactions are catalyzed by chiral squaramides and afford adducts in high yields (90-99%) and with excellent enantioselectivities (85-98%). The addition products are unmasked to produce dicyanohydrins that, upon treatment with a variety of nucleophiles, provide γ-keto acids, esters, and amides. The use of this umpolung synthon has enabled, in enantiomerically enriched form, the first total synthesis of the prenylated phenol (+)-fornicin C.
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