1078738-40-5Relevant academic research and scientific papers
First synthesis of enantiomerically pure (1S,2S)- and (1R,2R)-1,2-diaminocyclobutanecarboxylic acid-ornithine derivative-, from racemic 2-aminocyclobutanone
Hazelard, Damien,Fadel, Antoine,Guillot, Regis
, p. 2063 - 2067 (2008)
An easy and efficient one-pot reaction from readily available 2-(N-Cbz) aminocyclobutanone selectively gave, by means of an asymmetric Strecker synthesis in the presence of a chiral benzylic amine, the thermodynamic 1,2-diamino nitriles. Basic hydrolysis, cleavage of the benzylic group and acidic hydrolysis of the resulting trans-1,2-diaminocyclobutanecarbonitrile gave, in a four-step sequence from the ketone, (1S,2S)- or (1R,2R)-1,2-diaminocyclobutanecarboxylic acid, ornithine derivatives. The absolute configuration has been established by X-ray analysis of the corresponding trans-diamino amide.
