First synthesis of enantiomerically pure (1S,2S)- and (1R,2R)-1,2-diaminocyclobutanecarboxylic acid–ornithine derivative–, from racemic 2-aminocyclobutanone |
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Authors: | Damien Hazelard Antoine Fadel Rgis Guillot |
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Institution: | aLaboratoire de Synthèse Organique et Méthodologie, UMR 8182, Institut de Chimie Moléculaire et des Matériaux d’Orsay, Bât. 420, Université Paris-Sud, 91405 Orsay, France;bInstitut de Chimie Moléculaire et des Matériaux d’Orsay, Bât. 420, Université Paris-Sud, 91405 Orsay, France |
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Abstract: | 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. |
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