115378-34-2Relevant academic research and scientific papers
Synthesis of chiral, enantiopure allylic amines by the Julia olefination of α-amino esters
Benedetti, Fabio,Berti, Federico,Fanfoni, Lidia,Garbo, Michele,Regini, Giorgia,Felluga, Fulvia
, (2016/07/06)
The four-step conversion of a series of N-Boc-protected L-amino acid methyl esters into enantiopure N-Boc allylamines by a modified Julia olefination is described. Key steps include the reaction of a lithiated phenylalkylsulfone with amino esters, giving chiral β-ketosulfones, and the reductive elimination of related α-acetoxysulfones. The overall transformation takes place under mild conditions, with good yields, and without loss of stereochemical integrity, being in this respect superior to the conventional Julia reaction of α-amino aldehydes.
Copper-catalyzed tandem oxidation-olefination process
Davi, Michael,Lebel, Helene
supporting information; experimental part, p. 41 - 44 (2009/07/11)
A novel catalytic sequence aerobic oxidation-olefination has been developed. A single and inexpensive copper catalyst provides a large range of olefins from alcohols in good to excellent yields. The reaction exhibits excellent functional group compatibili
NOVEL CATHEPSIN C INHIBITORS AND THEIR USE
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Page/Page column 93, (2009/04/25)
The invention is directed to compounds according to Formula (I) wherein R1, R2a, R2b, R2c, R3, and n are defined below, and to pharmaceutically-acceptable salts thereof. They are cathepsin C inhibitors and can be used in the treatment of diseases mediated
Design, synthesis, and SAR of macrocyclic tertiary carbinamine BACE-1 inhibitors
Lindsley, Stacey R.,Moore, Keith P.,Rajapakse, Hemaka A.,Selnick, Harold G.,Young, Mary Beth,Zhu, Hong,Munshi, Sanjeev,Kuo, Lawrence,McGaughey, Georgia B.,Colussi, Dennis,Crouthamel, Ming-Chih,Lai, Ming-Tain,Pietrak, Beth,Price, Eric A.,Sankaranarayanan, Sethu,Simon, Adam J.,Seabrook, Guy R.,Hazuda, Daria J.,Pudvah, Nicole T.,Hochman, Jerome H.,Graham, Samuel L.,Vacca, Joseph P.,Nantermet, Philippe G.
, p. 4057 - 4061 (2008/02/10)
This Letter describes the design and synthesis of tertiary carbinamine macrocyclic inhibitors of the β-secretase (BACE-1) enzyme. These macrocyclic inhibitors, some of which incorporate novel P2 substituents, display a 2- to 100-fold increase in potency r
Improved synthesis of chiral N-protected allylic amines
Wei,Knaus
, p. 1463 - 1466 (2007/10/02)
The α-ester group of N-protected α-amino esters was reduced with diisobutylaluminum hydride to an intermediate aluminoxy acetal that on reaction with a Wittig reagent afforded the title chiral compounds in 48-78% chemical yields.
Synthesis of the Chiral (8S)-7-Aza-1,3(E),9-decatriene System from Natural α-Amino Acids and Its Intramolecular Diels-Alder Reaction Directed toward Chiral trans-Hydroisoquinolones
Moriwake, Toshio,Hamano, Shin-ich,Saito, Seiki,Torii, Shigeru,Kashino, Setsuo
, p. 4114 - 4120 (2007/10/02)
L-Alanine and L-valine were converted into optically active 7-aza-1,3(E),9-decatrienes containing a (tert-butyldimethylsilyl)oxy group at C(2) and a methyl or isopropyl group at C(8).Intramolecular thermal cycloaddition reactions of these trienes gave optically active trans-nonahydro-6(2H)-isoquinolones.The relatively bulky isopropyl group at C(8) increased the trans selectivity in the ring closure.These results are in contrast with literature reports on ring closure of analogous aza trienes that lack the (tert-butyldimethylsilyl)oxy group at C(2), whichgive predominantly cis-fused rings.
A Straightforward Synthesis of Allyl Amines from α-Amino Acids without Racemization
Moriwake, Toshio,Hamano, Shin-ichi,Saito, Seiki,Torii, Sigeru
, p. 2085 - 2088 (2007/10/02)
An extremely simple and practical synthesis of allyl amine derivatives from α-amino acids has been developed involving aldehyde olefination pathway with AlMe3-Zn-CH2I2 reagent which has proven to be crucial for preservation of stereochemical integrity.
