111060-70-9Relevant articles and documents
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.
Iodomethylation of Chiral α-Amino Aldehydes by Means of Samarium/Diiodomethane. Application to the Synthesis of Various Enantiomerically Pure Compounds
Concellon, Jose M.,Bernad, Pablo L.,Perez-Andres, Juan A.
, p. 8902 - 8906 (2007/10/03)
Chiral iodohydrins 2 have been obtained from α-amino aldehydes 1 and Sm/CH2I2. Treatment of compound 2 with acetic anhydride, NaH, or AgBF4 affords, with high diastereoselectivity, O-protected 3-(dibenzylamino)-1-iodoalkan-2-ol 3, amino epoxides 4, or azetidinium salts 5, respectively. The synthesis of enantiomerically pure allylamines 6 is also described by metallation of 3 with zinc. The reaction of α-amino aldehydes 1 with Sm/CH2I2 and further treatment with organocuprates affords chiral amino alcohols 7 in a one-pot process.
PROTECTIVE GROUP TUNING IN THE STEREOSELECTIVE CONVERSION OF α-AMINO ALDEHYDES INTO AMINOALKYL EPOXIDES
Reetz, M.T.,Binder, J.
, p. 5425 - 5428 (2007/10/02)
Sulfonium and arsonium ylides of the type CH2=S(CH3)2 and CH2=As(Ph)3 react with doubly protected α-amino aldehydes 1 derived from amino acids to form aminoalkyl epoxides 3/4, diastereofacial selectivity ranging between 86:14 and >95:5.
