908129-84-0Relevant academic research and scientific papers
Diastereoselective syntheses of 2-amino propargyl alcohols. Chiral building blocks for enantiopure amino γ-lactones and 5-hydroxy-piperidinone derivatives
Andrés, José María,Pedrosa, Rafael,Pérez-Encabo, Alfonso
, p. 5317 - 5320 (2006)
α-Dibenzylamino aldehydes, derived from the corresponding natural α-amino acids, react with metal acetylides to yield anti-amino propargyl alcohols in good yield and diastereomeric excess. syn Amino alcohols are prepared from the anti diastereoisomers and
Direct stereoselective synthesis of enantiomerically pure anti -β-amino alcohols
Silveira-Dorta, Gastón,Donadel, Osvaldo J.,Martín, Víctor S.,Padrón, José M.
, p. 6775 - 6782 (2014/08/18)
Enantiomerically pure anti-β-amino alcohols were synthesized from optically pure α-(N,N-dibenzylamino)benzyl esters, derived from α-amino acids, by the sequential reduction to aldehyde with DIBAL-H at -78 °C and subsequent in situ addition of Grignard reagents. Besides anti-β-amino alcohols, anti-2-amino-1,3-diols and anti-3-amino-1,4-diols were obtained in good yields (60-95%) and excellent stereoselectivity (de > 95%). Our technique is compatible with free hydroxyl groups present in the substrate. To demonstrate the versatility of the method, spisulosine and sphinganine were synthesized in two steps from the appropriate N,N-dibenzyl-l-aminobenzyl ester in 42% and 45% yield, respectively.
Diastereoselective ethynylation of chiral α-(dibenzylamino) aldehydes: Synthesis of meso- and homochiral C2-symmetrical 1,6-diamino-2,5-diols
Andrés, José M.,Pedrosa, Rafael,Pérez-Encabo, Alfonso
, p. 3442 - 3450 (2007/10/03)
Homochiral α-(dibenzylamino) aldehydes, prepared from the corresponding α-amino acids, react with ethynylmagnesium bromide in THF/Et2O at 0°C to afford, in good yields and dr, propargylic 1,2-amino alcohols; anti diastereomers were always forme
