ArticleJournal of the American Chemical Society2014
Synthesis of α-amino acid derivatives and peptides via enantioselective addition of masked acyl cyanides to imines.
Article in Journal of the American Chemical Society, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 12 papers.
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Who cites it
12 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
- Molybdenum-Catalyzed Asymmetric Amination of α-Hydroxy Esters: Synthesis of α-Amino Acids.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2025Article
- 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
- Enantioselective organocatalytic strategies to access noncanonical α-amino acids.Chemical science · 2024Review
- Asymmetric Catalytic Friedel-Crafts Reactions of Unactivated Arenes.Journal of the American Chemical Society · 2023Article
- 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
- Total Synthesis of Tagetitoxin.Journal of the American Chemical Society · 2020Article
- Intermolecular Stereoselective Iridium-Catalyzed Allylic Alkylation: An Evolutionary Account.Synlett : accounts and rapid communications in synthetic organic chemistry · 2018Article
- 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
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Abstract
A general, asymmetric synthesis of amino acid derivatives is reported. Masked acyl cyanide (MAC) reagents are shown to be effective umpolung synthons for enantioselective additions to N-Boc-aldimines. The reactions are catalyzed by a modified cinchona alkaloid, which can function as a bifunctional, hydrogen bonding catalyst, and afford adducts in excellent yields (90-98%) and high enantioselectivities (up to 97.5:2.5 er). Unmasking the addition products gives acyl cyanide intermediates that are intercepted by a variety of nucleophiles to afford α-amino acid derivatives. Notably, the methodology provides an alternative method for peptide bond formation.
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