Literature DB >> 23245626

2-Aryl-2-nitroacetates as central precursors to aryl nitromethanes, α-ketoesters, and α-amino acids.

Alison E Metz1, Marisa C Kozlowski.   

Abstract

Nitroarylacetates are useful small molecular building blocks that act as precursors to α-ketoesters and aryl nitromethanes as well as α-amino acids. Methods were developed that produce each of these compound types in good yields. Two different conditions for decarboxylation are discussed for substrates with neutral and electron-poor aryl groups versus electron-rich aryl groups. For formation of the α-ketoesters, new mild conditions for the Nef disproportionation were identified.

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Year:  2013        PMID: 23245626      PMCID: PMC3548967          DOI: 10.1021/jo302071s

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  22 in total

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2.  Ambident reactivity of the nitrite ion revisited.

Authors:  Alexander A Tishkov; Uli Schmidhammer; Stefan Roth; Eberhard Riedle; Herbert Mayr
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3.  Relaxometric and modelling studies of the binding of a lipophilic Gd-AAZTA complex to fatted and defatted human serum albumin.

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4.  Kinetic study of proton-transfer reactions of phenylnitromethanes. Implication for the origin of nitroalkane anomaly.

Authors:  Kenichi Ando; Yu Shimazu; Natsuko Seki; Hiroshi Yamataka
Journal:  J Org Chem       Date:  2011-04-12       Impact factor: 4.354

5.  Synthesis and biological evaluation of benzoic acid derivatives as potent, orally active VLA-4 antagonists.

Authors:  Jun Chiba; Shin Iimura; Yoshiyuki Yoneda; Toshiyuki Watanabe; Fumito Muro; Masao Tsubokawa; Yutaka Iigou; Atsushi Satoh; Gensuke Takayama; Mika Yokoyama; Tohru Takashi; Atsushi Nakayama; Nobuo Machinaga
Journal:  Bioorg Med Chem       Date:  2006-12-09       Impact factor: 3.641

6.  Highly enantioselective synthesis of α,α-dialkylmalonates by phase-transfer catalytic desymmetrization.

Authors:  Suckchang Hong; Jihye Lee; Minsik Kim; Yohan Park; Cheonhyoung Park; Mi-hyun Kim; Sang-sup Jew; Hyeung-geun Park
Journal:  J Am Chem Soc       Date:  2011-03-09       Impact factor: 15.419

7.  Asymmetric cyanation of aldehydes, ketones, aldimines, and ketimines catalyzed by a versatile catalyst generated from cinchona alkaloid, achiral substituted 2,2'-biphenol and tetraisopropyl titanate.

Authors:  Jun Wang; Wentao Wang; Wei Li; Xiaolei Hu; Ke Shen; Cheng Tan; Xiaohua Liu; Xiaoming Feng
Journal:  Chemistry       Date:  2009-11-02       Impact factor: 5.236

8.  Rapid decarboxylative allylation of nitroalkanes.

Authors:  Alexander J Grenning; Jon A Tunge
Journal:  Org Lett       Date:  2010-02-19       Impact factor: 6.005

9.  Ag-catalyzed diastereo- and enantioselective vinylogous Mannich reactions of alpha-ketoimine esters. Development of a method and investigation of its mechanism.

Authors:  Laura C Wieland; Erika M Vieira; Marc L Snapper; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2009-01-21       Impact factor: 15.419

10.  Peptide alpha-keto ester, alpha-keto amide, and alpha-keto acid inhibitors of calpains and other cysteine proteases.

Authors:  Z Li; G S Patil; Z E Golubski; H Hori; K Tehrani; J E Foreman; D D Eveleth; R T Bartus; J C Powers
Journal:  J Med Chem       Date:  1993-10-29       Impact factor: 7.446

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  1 in total

1.  Palladium-Catalyzed α-Arylation of Aryl Nitromethanes.

Authors:  Kelsey F VanGelder; Marisa C Kozlowski
Journal:  Org Lett       Date:  2015-11-20       Impact factor: 6.005

  1 in total

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