160002-54-0Relevant academic research and scientific papers
Synthesis and photochemical decomposition of pyrazolines from homochiral amino pentenoates. A laser flash-photolysis study
Jimenez, Jose M.,Bourdelande, Jose L.,Ortuno, Rosa M.
, p. 3777 - 3786 (2007/10/03)
Optically pure pyrazolines have been synthesized by cycloaddition of diazomethane to homochiral amino pentenoates, facial diastereoselectivity being the opposite depending on the Z/E stereochemistry of the precursors. Photo-decomposition of these pyrazolines to the corresponding cyclopropanes has been shown to occur stereospecifically and has been studied in order to find the optimal conditions and to establish the influence of sensitizers. The transient behaviour of the pyrazoline triplet state has been analyzed by laser flash photolysis either after direct excitation or after energy transfer from benzophenone.
Enantioselective total syntheses of cyclopropane amino acids: Natural products and protein methanologs
Jimenez, Jose M.,Rife, Joan,Ortuno, Rosa M.
, p. 537 - 558 (2007/10/03)
The syntheses of (-)-allo-coronamic acid, (-)-allo-norcoronamic acid, (-)-(Z)-2,3-methanohomoserine, (-)-(Z)-2,3-methanomethionine, and (2S,3R)-Cbz-cyclo-Asp-OMe have been achieved in 45-68% overall yields from suitable intermediates derived from homochiral aminopentenoates which were obtained, in turn, from D-glyceraldehyde. The key synthetic step involves the quantitative and highly diastereoselective cyclopropanation of such precursors. The factors dealing with the control of stereoselectivity are highlighted and the main features in side-chain functionalization to the respective target molecules are discussed.
Enantioselective Total Syntheses of (-)-allo-Coronamic Acid, (-)-(Z)-2,3-Methanohomoserine, and (2S,3R)-Cbz-cyclo-Asp-OMe
Jimenez, Jose M.,Rife, Joan,Ortuno, Rosa M.
, p. 1849 - 1852 (2007/10/03)
The title amino acids have been synthesized in 45, 47, and 63percent overall yields, respectively, from enantiopure aminopentenoates, easily available from D-glyceraldehyde as a source of chirality, following divergent pathways from similar diols as commo
Highly efficient and stereocontrolled synthetic route to enantiopure ACC derivatives: Synthesis of (+)-N-benzyloxycarbonyl-γ,δ-dehydro-allo-coronamic acid methyl ester
Jimenez, Jose M.,Casas, Ramon,Ortuno, Rosa M.
, p. 5945 - 5948 (2007/10/02)
Highly diastereoselective cyclopropanation of a chiral α,β-dehydroamino acid derivative, obtained from D-mannitol, leads to a single isomer which has been transformed into the title compound in 65% overall yield. This product can be a useful intermediate
