18944-00-8Relevant academic research and scientific papers
Benzoazepine-Fused Isoindolines via Intramolecular (3 + 2)-Cycloadditions of Azomethine Ylides with Dinitroarenes
Wales, Steven M.,Rivinoja, Daniel J.,Gardiner, Michael G.,Bird, Melissa J.,Meyer, Adam G.,Ryan, John H.,Hyland, Christopher J. T.
supporting information, p. 4703 - 4708 (2019/06/27)
Aminobenzaldehydes bearing a pendant 3,5-dinitrophenyl group react thermally with N-substituted α-amino acids to form unprecedented benzoazepine-fused isoindolines. The reaction proceeds via a dearomatization/rearomatization sequence involving an intramolecular (3 + 2)-cycloaddition between the in situ formed azomethine ylide and the dinitroarene. Various glycine derivatives are tolerated as well as branched substrates based on cyclic, α-mono-, and α,α-disubstituted amino acids, giving single diastereomers in many cases. The method is scalable and gives products with a nitro group ready for further manipulation.
Diastereoselective synthesis of quaternary α-amino acids from diketopiperazine templates
Davies, Stephen G.,Christopher Garner,Ouzman, Jaqueline V. A.,Roberts, Paul M.,Smith, Andrew D.,Snow, Emma J.,Thomson, James E.,Tamayo, Juan A.,Vickers, Richard J.
, p. 2138 - 2147 (2008/03/14)
Sequential enolate alkylations of (S)-N(1)-methyl-5-methoxy-6-isopropyl-3, 6-dihydropyrazin-2-one and (S)-N(1)-p-methoxybenzyl-5-methoxy-6-isopropyl-3,6- dihydropyrazin-2-one proceed with excellent levels of diastereoselectivity (>90% de) affording quaternary α-amino acids in high enantiomeric excess (>98% ee) after deprotection and hydrolysis. This journal is The Royal Society of Chemistry.
An efficient synthesis of N-methylamino acids and some of their derivatives
Spengler, Jan,Burger, Klaus
, p. 67 - 70 (2007/10/03)
N-Methylamino acid derivatives are obtained in high yield by a stereoselective one-pot procedure from hexafluoroacetone protected amino acids via N-chloromethylation and treatment with triethylsilane/trifluoroacetic acid.
Asymmetric amino acid synthesis: Mitsunobu reaction on chiral cyanohydrins
Decicco, Carl P.,Grover, Paul
, p. 529 - 530 (2007/10/03)
BOC(SES)NH was reacted with chiral cyanohydrins using the Mitsunobu reaction to give good yields of protected α-aminonitriles, which were converted to chiral amino and imino acids.
