117997-58-7Relevant articles and documents
New approaches to the asymmetric synthesis of dipeptide isosteres via β-Lactam Synthon Method
Ojima, Iwao,Wang, Hong,Wang, Tao,Ng, Edward W.
, p. 923 - 926 (2007/10/03)
New and efficient synthetic routes to dipeptide isosteres with high enantiomeric purity, e.g., hydroxyethylene, dihydroxyethylene and hydroxyethylamine isosteres, have been developed via oxiranes 6 and formyloxazolines 13 derived from N-t-Boc-β-lactams 4.
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.
STEREOSELECTIVE SYNTHESIS OF A C-TERMINAL COMPONENT OF RENIN INHIBITORS VIA ITERATIVE HOMOLOGATION
Wagner, Adalbert,Mollath, Martina
, p. 619 - 622 (2007/10/02)
A stereoselective synthesis of an aminodiol derivative (dipeptide mimic) has been developed via iterative homologation of protonated cyclohexylalaninal (Dondoni reaction).
