182121-96-6Relevant academic research and scientific papers
FeCl3: Highly efficient catalyst for synthesis of α-amino nitriles
Heravi, Majid M,Ebrahimzadeh, Mojgan,Oskooie, Hossein A,Baghernejad, Bita
, p. 480 - 482 (2010)
α-Amino nitriles are synthesized by the three-component coupling reaction of aldehydes, amines and trimethylsilyl cyanide using FeCl3 as a solid acid catalyst, under solvent-free conditions in good yields. The catalyst was recovered by simple f
Sulfonium ion-promoted traceless Schmidt reaction of alkyl azides
Ardiansah, Bayu,Kakiuchi, Kiyomi,Morimoto, Tsumoru,Tanimoto, Hiroki,Tomohiro, Takenori
, p. 8738 - 8741 (2021/09/08)
Schmidt reaction by sulfonium ions is described. General primary, secondary, and tertiary alkyl azides were converted to the corresponding carbonyl or imine compounds without any trace of the activators. This bond scission reaction through 1,2-migration of C-H and C-C bonds was accessible to the one-pot substitution reaction.
The direct synthesis of unsymmetrical vicinal diamines from terminal alkynes: A tandem sequential approach for the synthesis of imidazolidinones
Lee, Alison V.,Sajitz, Melanie,Schafer, Laurel L.
experimental part, p. 97 - 104 (2009/07/18)
The combination of titanium-catalyzed anti-Markovni- kov hydroamination of terminal alkynes with the Strecker reaction is used in the synthesis of unsymmetrical vicinal diamines via the one-pot synthesis of α-cyanoamines. This methodology is further applied to the efficient synthesis of imidazolidinones. An easy-to-use bis(amidate)titanium precatalyst permits efficient approaches to heterocyclic chemistry from terminal alkynes. Georg Thieme Verlag Stuttgart.
A sequential C-N, C-C bond-forming reaction: Direct synthesis of α-amino acids from terminal alkynes
Lee, Alison V.,Schafer, Laurel L.
, p. 2973 - 2976 (2008/03/11)
Catalytic hydroamination is combined with the Strecker reaction to yield a one-pot synthesis of α-cyanoamines from terminal alkynes. This methodology is further applied to the synthesis of α-amino acids and α-amino esters. Georg Thieme Verlag Stuttgart.
Asymmetric synthesis of 3-amino-2-hydroxy-4-phenylbutanoate
Ha, Hyun-Joon,Ahn, Young-Gil,Lee, Gwan Sun
, p. 2327 - 2336 (2007/10/03)
Asymmetric synthesis of 3-amino-2-hydroxy-4-phenylbutanoate, a key component of the natural product bestatin and HIV protease inhibitors of KNI- 272 and R-87366, has been achieved from the stereoselective aldimine coupling reaction between 3-phenyl-2-aminopropanenitrile and (Z)-α-methoxy trimethylsilyl ketene acetal in the presence of Lewis acids.
Syntheses of optically active α-amino nitrites by asymmetric transformation of the second kind using a principle of O. Dimroth
Hassan, Nasser A.,Bayer, Erwin,Jochims, Johannes C.
, p. 3747 - 3757 (2007/10/03)
A mixture of solids As and Bs in equilibrium with the dissolved compounds A1 and B1 is transformed completely into one pure solid, say Bs, if the dissolved compounds A1?B1 are equilibrating in solution. This is applied to transform 1:1 mixtures of solid diastereomeric amygdalates (2-hydroxy-2-phenylacetates; mandelates) (R,R)-3 + (S,R)-3 prepared from racemic α-amino nitriles (R,S)-1 with (R)-mandelic acid 2 into stereochemically pure single diastereomers (R,R)-3, or (S,R)-3 (de > 97%) ('asymmetric transformation of the second kind by application of Dimroth's principle'). Decomposition of the amygdalates (R,R)-3, or (S,R)-3, with aqueous base affords the enantiomerically pure α-amino nitriles (A)-1, or (S)-1 (ten examples). The chiral auxiliary (R)-mandelic acid is recovered almost quantitatively. The optically active α-amino nitriles are hydrolyzed to amides 6, and further to α-N-alkylamino acids 7. N-Benzylamino acids 7 are hydrogenated to α-amino acids 8. Some of the optically active α-amino nitriles 1 are reduced to optically active 1,2-diamines 9. In most cases, absolute configurations could be assigned by comparison of the specific rotations observed with those of authentic compounds.
