308266-24-2Relevant academic research and scientific papers
Ti(II)-mediated conversion of α-heterosubstituted (O, N, S) nitriles to functionalized cyclopropylamines. Effect of chelation on the cyclopropanation step
Bertus, Philippe,Szymoniak, Jan
, p. 3965 - 3968 (2007/10/03)
α-Alkoxy, amino-, and thio nitriles undergo a Ti(II)-mediated coupling with Grignard reagents to afford heterofunctionalized cyclopropylamines. A chelation effect appears to be generally responsible for the spontaneous contraction of the intermediate azatitanacycle leading to cyclopropane. By using the described reaction, 1-aminocyclopropanecarboxylic acids were prepared in four steps, in good overall yields, from the readily available benzyloxyacetonitrile.
Cyclopropyl building blocks for organic synthesis, 58(+): A new short access to amino acids incorporating an aminocyclopropyl moiety from N,N-dibenzylcarboxamides
Kordes, Markus,Winsel, Harald,De Meijere, Armin
, p. 3235 - 3245 (2007/10/03)
Our recently reported titanium-mediated transformation of N,N-dialkylcarboxamides to cyclopropylamines has been applied to N,N-dibenzyl-2-benzyloxyacetamide using a variety of alkylmagnesium bromides to yield 1-(benzyloxymethyl)-1-(dibenzylamino)cyclopropane (15a, 48percent) and 2-substituted analogs 15b-f (33-48percent). These have been transformed in just a few steps into N-Boc-protected methyl esters of 1-aminocyclopropanecarboxylic acid (1, 29percent overall), coronamic acid (2, 35percent) and norcoronamic acid (21percent), 2,3-methanoglutamic acid (21g, 19percent) and 2,3-methanoornithine (211, 12percent). Similarly, the corresponding derivatives of 3,4-methano-γ-aminobutyric acid (26, 23percent) and 4-spirocyclopropane-γ-butyrolactam (32, 44percent) have been synthesized.
