187818-08-2Relevant articles and documents
Stereocontrolled synthesis of pseudo C2-symmetric 1,3-diamino-2-propanol core units of HIV protease inhibitors
Dondoni, Alessandro,Perrone, Daniela
, p. 499 - 502 (1997)
The synthesis of the pseudo C2-symmetric dibenzyldiamino alcohol (S,S)-1 and the two meso stereoisomers 1a and 1b (R = PhCH2) is described by stereocontrolled benzylmagnesium chloride addition to the nitrones 3 derived from chiral β-amino-α-hydroxy aldehydes 2 that in turn were obtained from phenylalanino; the overall yield of (S,S)-1 is 23% from N-Boc L-phenylalaninal; the antipode (R,R)-1 can be prepared in a similar way starting from the D-isomer of the same α-amino aldehyde.
Grignard addition to aldonitrones. Stereochemical aspects and application to the synthesis of C2-symmetric diamino alcohols and diamino diols
Dondoni, Alessandro,Perrone, Daniela,Rinaldi, Marilisa
, p. 9252 - 9264 (2007/10/03)
A new example of the stereoselective installation of the amino group at a saturated carbon center via organometallic addition of chiral aldehydes to nitrones is illustrated by the synthesis of 1,3-diamino propanol 1 and 1,4- diamino butandiol 2 units. Three diamino alcohol 1 stereotriads were obtained by stereoselective addition of alkylmagnesium halides (benzyl, cyclohexylmethyl, and metallyl) to the N-benzyl nitrones derived from β- amino-α-hydroxy aldehydes followed by reduction of the resulting N- benzylhydroxylamines. Three 1,4-dibenzyl substituted stereoisomers of type 2 with fixed S configuration at C2 and C3 were prepared by sequential and simultaneous amination in two directions starting from L-threose nitrone and L-tartraldehyde bis-nitrone, respectively. The R,S,S,R isomer obtained by the former route was converted into a seven-membered ring cyclic urea (1,3- diazapin-2-one), i.e., a compound that belongs to a class of nonpeptide HIV- 1 protease inhibitors.
