Literature DB >> 16231887

A highly efficient carbon-carbon bond formation reaction via nucleophilic addition to N-alkylaldimines without acids or metallic species.

Hisao Nemoto1, Tomoyuki Kawamura, Norikazu Miyoshi.   

Abstract

A nucleophilic addition reaction to N-methylaldimines without acid or metal species is described. A novel reagent, dicyanomethyl acetate, is used as a nucleophile to give alpha-(N-methyl-N-acetyl)amino acid methyl esters in excellent yield.

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Year:  2005        PMID： 16231887     DOI： 10.1021/ja054010h

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  6 in total

1.  Enantioselective Iridium-Catalyzed Allylic Alkylation Reactions of Masked Acyl Cyanide Equivalents.

Authors:  J Caleb Hethcox; Samantha E Shockley; Brian M Stoltz
Journal:  Org Lett       Date:  2017-03-14       Impact factor: 6.005

2.  Intermolecular Stereoselective Iridium-Catalyzed Allylic Alkylation: An Evolutionary Account.

Authors:  Samantha E Shockley; J Caleb Hethcox; Brian M Stoltz
Journal:  Synlett       Date:  2018-08-15       Impact factor: 2.454

3.  Exploiting hidden symmetry in natural products: total syntheses of amphidinolides C and F.

Authors:  Subham Mahapatra; Rich G Carter
Journal:  J Am Chem Soc       Date:  2013-07-11       Impact factor: 15.419

4.  Elucidating the Supramolecular Copolymerization of N- and C-Centered Benzene-1,3,5-Tricarboxamides: The Role of Parallel and Antiparallel Packing of Amide Groups in the Copolymer Microstructure.

Authors:  Lafayette N J de Windt; Zulema Fernández; Manuel Fernández-Míguez; Félix Freire; Anja R A Palmans
Journal:  Chemistry       Date:  2021-12-02       Impact factor: 5.020

5.  Squaramide-catalyzed enantioselective Michael addition of masked acyl cyanides to substituted enones.

Authors:  Kin S Yang; Antoinette E Nibbs; Yunus E Türkmen; Viresh H Rawal
Journal:  J Am Chem Soc       Date:  2013-10-17       Impact factor: 15.419

6.  Ruthenium(ii)-catalyzed regioselective 1,6-conjugate addition of umpolung aldehydes as carbanion equivalents.

Authors:  Hyotaik Kang; Chao-Jun Li
Journal:  Chem Sci       Date:  2021-11-29       Impact factor: 9.825
  6 in total

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