65130-83-8Relevant academic research and scientific papers
Enantioselective Synthesis of α-Aryl-β2-Amino-Esters by Cooperative Isothiourea and Br?nsted Acid Catalysis
Zhao, Feng,Shu, Chang,Young, Claire M.,Carpenter-Warren, Cameron,Slawin, Alexandra M. Z.,Smith, Andrew D.
, p. 11892 - 11900 (2021/04/28)
The synthesis of α-aryl-β2-amino esters through enantioselective aminomethylation of an arylacetic acid ester in high yields and enantioselectivity via cooperative isothiourea and Br?nsted acid catalysis is demonstrated. The scope and limitatio
Forming All-Carbon Quaternary Stereocenters by Organocatalytic Aminomethylation: Concise Access to β2,2-Amino Acids
Shao, Ying,Sun, Jiangtao,Tang, Shengbiao,Wang, Kai,Yu, Jianliang
supporting information, p. 23516 - 23520 (2020/10/21)
The asymmetric synthesis of β2,2-amino acids remains a formidable challenge in organic synthesis. Here a novel organocatalytic enantioselective aminomethylation of ketenes with stable and readily available N,O-acetals is reported, providing β2,2-amino esters bearing an all-carbon quaternary stereogenic center in high enantiomeric ratios with a catalytic amount of chiral phosphoric acid. Typically, this transformation probably proceeds through an asymmetric counter-anion-directed catalysis. As a result, a concise, practical, and atom-economic protocol toward rapidly access to β2,2-amino acids has been developed.
Asymmetric Counter-Anion-Directed Aminomethylation: Synthesis of Chiral β-Amino Acids via Trapping of an Enol Intermediate
Kang, Zhenghui,Wang, Yongheng,Zhang, Dan,Wu, Ruibo,Xu, Xinfang,Hu, Wenhao
supporting information, p. 1473 - 1478 (2019/01/26)
A novel enantioselective aminomethylation reaction of diazo compound, alcohol and α-aminomethyl ether enabled by asymmetric counteranion-directed catalysis is disclosed that offers an efficient and convenient access to furnish optically active α-hydroxyl-β-amino acids in high yield with high to excellent enantioselectivities. Control experiments and DFT calculations indicate that the transformation proceeds through trapping the in situ generated enol intermediate with methylene iminium ion, and the asymmetric induction was enabled by chiral pentacarboxycyclopentadiene anion via H-bonding and electrostatic interaction.
A General Acid-Mediated Hydroaminomethylation of Unactivated Alkenes and Alkynes
Kaiser, Daniel,Tona, Veronica,Gon?alves, Carlos R.,Shaaban, Saad,Oppedisano, Alberto,Maulide, Nuno
, p. 14639 - 14643 (2019/09/17)
In comparison to the extensively studied metal-catalyzed hydroamination reaction, hydroaminomethylation has received significantly less attention despite its considerable potential to streamline amine synthesis. State-of-the-art protocols for hydroaminomethylation of alkenes rely largely on transition-metal catalysis, enabling this transformation only under highly designed and controlled conditions. Here we report a broadly applicable, acid-mediated approach to the hydroaminomethylation of unactivated alkenes and alkynes. This methodology employs cheap, readily available, and bench-stable reactants and affords the desired amines with excellent functional group tolerance and impeccable regioselectivity. The broad scope of this transformation, as well as mechanistic investigations and in situ domino functionalization reactions are reported.
Synthesis of monofluoro- and difluoro- methylenephosphonate analogues of sn-glycerol-3-phosphate as substrates for glycerol-3-phosphate dehydrogenase and the X-ray structure of the fluoromethylenephosphonate moiety
Nieschalk, Jens,Batsanov, Andrei S.,O'Hagan, David,Howard, Judith A. K.
, p. 165 - 176 (2007/10/02)
The synthesis of the cyclohexylammonium salts of (1RS, 3S)-3,4-dihydroxy-1-fluorobutylphosphonic acid 3 and (S)-difluoro-3,4-dihydroxybutylphosphonic acid 4 is reported. These compounds are fluorinated phosphonate analogues of sn-glycerol-3-phosphate wher
Acyl Halide Induced Cleavage of N-Acylated Aminals
Boehme, Horst,Raude, Edgar
, p. 3421 - 3429 (2007/10/02)
Acyl halides attack N-acylated aminals 6 at the amine nitrogen as well as at the carboxamide group to form either N-halomethyl carboxamides 5 besides N,N-dialkyl carboxamides 11, or diacylamines 12 besides N,N-dialkylmethaneiminium halides 4.Depending on the variation of the substituents on both heteroatoms the cleavage may be directed to follow only one or the other pathway.Of highly synthetic interest is the broadly applicable preparation of methaneiminium salts 4 having bulky substituents on nitrogen by means of cleavage of the corresponding N,N-dialkyl-N'-formyl-N'-methylmethanediamines 6.
