Preparation of One-Carbon Homologated Amides from Aldehydes or Primary Alcohols

被引:37
作者
Gupta, Manoj K. [1 ]
Li, Zhexi [1 ]
Snowden, Timothy S. [1 ]
机构
[1] Univ Alabama, Dept Chem, Tuscaloosa, AL 35487 USA
基金
美国国家科学基金会;
关键词
METHOXY-N-METHYLAMIDES; ALPHA-HYDROXY ACIDS; CARBOXYLIC-ACIDS; ENANTIOSELECTIVE SYNTHESIS; TRICHLOROMETHYL KETONES; ARYL ALDEHYDES; CONVERSION; ESTERS;
D O I
10.1021/ol500200n
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Aldehydes and primary alcohols can be converted to one-carbon homologated primary, secondary, or tertiary amides in two operational steps. The approach offers several unique features including compatibility with (hetero)-aryl, alkyl, alkenyl, and racemizable chiral substrates, the ability to prepare Weinreb amides from aryl and unhindered aliphatic substrates, and the opportunity to employ unprotected amino acids as amine sources in the amidation step.
引用
收藏
页码:1602 / 1605
页数:4
相关论文
共 48 条
  • [31] Asymmetric Synthesis of N-Substituted 1,2-Amino Alcohols from Simple Aldehydes and Amines by One-Pot Sequential Enzymatic Hydroxymethylation and Asymmetric Reductive Amination
    Li, Yu
    Hu, Na
    Xu, Zefei
    Cui, Yunfeng
    Feng, Jinhui
    Yao, Peiyuan
    Wu, Qiaqing
    Zhu, Dunming
    Ma, Yanhe
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2022, 61 (17)
  • [32] Scientific Opinion on Flavouring Group Evaluation 06, Revision 2 (FGE.06Rev2): Straight- and branched-chain aliphatic unsaturated primary alcohols, aldehydes, carboxylic acids, and esters from chemical groups 1 and 4
    Anadon, Arturo
    Binderup, Mona-Lise
    Bursch, Wilfried
    Castle, Laurence
    Crebelli, Riccardo
    Engel, Karl-Heinz
    Franz, Roland
    Gontard, Nathalie
    Haertle, Thomas
    Husoy, Trine
    Jany, Klaus-Dieter
    Leclercq, Catherine
    Lhuguenot, Jean Claude
    Mennes, Wim
    Milana, Maria Rosaria
    Pfaff, Karla
    Svensson, Kenji
    Toldra, Fidel
    Waring, Rosemary
    Wolfle, Detlef
    EFSA JOURNAL, 2011, 9 (03)
  • [35] Flavouring Group Evaluation 01, Revision 2 (FGE.01Rev2): Branched-chain aliphatic saturated aldehydes, carboxylic acids and related esters of primary alcohols and branched-chain carboxylic acids from chemical groups 1 and 2
    EFSA Panel on Food Contact Materials, Enzymes, Flavourings and Processing Aids
    EFSA JOURNAL, 2010, 8 (11)
  • [36] Flavouring Group Evaluation 2, Revision 1: Branched-and straight-chain aliphatic saturated primary alcohols and related esters of primary alcohols and straight-chain carboxylic acids and one straight-chain aldehyde from chemical groups 1 and 2 (Commission Regulation (EC) No 1565/2000 of 18 July 2000) 1 Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in contact with Food (AFC) on a request from the Commission
    Aguilar, Fernando
    Autrup, Herman
    Barlow, Susan
    Castle, Laurence
    Crebelli, Riccardo
    Dekant, Wolfgang
    Engel, Karl-Heinz
    Gontard, Nathalie
    Gott, David
    Grilli, Sandro
    Gurtler, Rainer
    Larsen, John Christian
    Leclercq, Catherine
    Leblanc, Jean-Charles
    Malcata, Xavier
    Mennes, Wim
    Milana, Maria Rosaria
    Pratt, Iona
    Rietjens, Ivonne
    Tobback, Paul
    Toldra, Fidel
    EFSA JOURNAL, 2008, 6 (05):
  • [37] One-pot synthesis of high-carbon bio-alcohols from aqueous ethanol upgrading over water-tolerance NiSn@C catalyst
    Liu, Wenping
    Chen, Bo
    Zhang, Qian
    Qiu, Songbai
    Wu, Xiaoping
    Meng, Qingwei
    Ma, Liang
    Wang, Tiejun
    ENERGY CONVERSION AND MANAGEMENT, 2021, 249
  • [38] Enhanced catalytic activity of cobalt nanoparticles encapsulated with an N-doped porous carbon shell derived from hollow ZIF-8 for efficient synthesis of nitriles from primary alcohols in water
    Sun, Kang-kang
    Sun, Jia-lin
    Lu, Guo-Ping
    Cai, Chun
    GREEN CHEMISTRY, 2019, 21 (16) : 4334 - 4340
  • [39] Synergistic atom co-sharing and S-scheme heterojunction: constructing Cu/CuO/Cu2O with ultrathin graphene-like carbon derived from basil seeds for enhanced photo-oxidation of benzyl alcohols to aldehydes
    Nalkyashree, Zahra Kohansal
    Koukabi, Nadiya
    Dashtian, Kheibar
    Seidi, Farzad
    NANOSCALE ADVANCES, 2024, 6 (21): : 5348 - 5360
  • [40] Consideration of linear and branched-chain aliphatic unsaturated, unconjugated alcohols, aldehydes, acids, and related esters evaluated by JECFA (61st meeting) structurally related to esters of branched- and straight-chain aliphatic saturated primary alcohols and of one secondary alcohol, and branched- and straight-chain unsaturated carboxylic acids evaluated by EFSA in FGE. 05 (2005) and to straight-and branched- chain aliphatic unsaturated primary alcohols, aldehydes, carboxylic acids, and esters evaluated by EFSA in FGE. 06 (2004) (Commission Regulation (EC) No 1565/2000 of 18 July 2000) Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in contact with Food (AFC) on a request from the Commission
    Aguilar, Fernando
    Autrup, Herman
    Barlow, Susan
    Castle, Laurence
    Crebelli, Riccardo
    Dekant, Wolfgang
    Engel, Karl-Heinz
    Gontard, Nathalie
    Gott, David
    Grilli, Sandro
    Gurtler, Rainer
    Larsen, John-Christian
    Leclercq, Catherine
    Leblanc, Jean-Charles
    Malcata, Xavier
    Mennes, Wim
    Milana, Maria-Rosaria
    Pratt, Iona
    Rietjens, Ivonne
    Tobback, Paul
    Toldra, Fidel
    EFSA JOURNAL, 2008, 6 (05):