161111-15-5Relevant academic research and scientific papers
Diastereo- and enantioselective synthesis of 2-substituted 1-aminocyclopropane-1-carboxylic acids. Application to the synthesis of protected 2,3-methano analogs of ornithine and glutamic acid
Frick, Jeffrey A.,Klassen, John B.,Rapoport, Henry
, p. 1751 - 1756 (2007/10/03)
An enantiodivergent synthesis of protected 2,3-methano amino acid analogs is described. (R)-2-benzyloxyethyloxirane, prepared from (S)-aspartic acid, was reacted with tert-butyl hydrogen malonate and further transformed into an enantiomeric pair of interm
Synthesis of (1R,3R,5S)-1-amino-3-(hydroxymethyl)bicyclo[3.1.0]hexane as a precursor for the synthesis of carbocyclic nucleosides
Chang,Bergmeier,Frick,Bathe,Rapoport
, p. 5336 - 5342 (2007/10/02)
The stereocontrolled synthesis has been achieved of a 1,5-methano-1-amino-5-(hydroxymethyl)cyclopentane, a potential component for carbocyclic nucleosides. Stereocontrol was manifest by converting (R)-2-((benzyloxy)ethyl)oxirane specifically to (2S,3S)-2-amino-2,3-methanoadipate through a series of lactones. This aminocyclopropanecarboxylate was then cyclized to the corresponding cyclopentanone ester. Reduction of the ketone, elimination, and hydrogenation of the double bond led primarily to the cyclopentane with the amino and ester groups trans (9/1). Enolization followed by an ammonium chloride quench then inverted this to a mixture in which the cis isomer was dominant (4/1). Simple functional group manipulation then gave the target (1R,3R,5S)-1-amino-3-(hydroxymethyl)bicyclo[3.1.0]hexane.
