132523-50-3Relevant academic research and scientific papers
Asymmetric synthesis of α- And β-amino acids by diastereoselective addition of triorganozincates to N-(tert-butanesulfinyl) imines
Almansa, Raquel,Collados, Juan F.,Guijarro, David,Yus, Miguel
experimental part, p. 1421 - 1431 (2010/11/02)
The diastereoselective addition of triorganozincates to (R)-N-(tert-butanesulfinyl)imines has been used as a key step to achieve the synthesis of highly enantiomerically enriched N-protected α- and β-amino acids. Desulfinylation of the addition products followed by benzoylation of the nitrogen atom of the obtained primary amines and oxidation of one of the substituents on the carbon atom connected to the nitrogen complete the sequence. Using the same configuration in the sulfinyl chiral auxiliary, α-amino acids with the (R) or the (S) configuration can be prepared by choosing the proper combination of imine and organozincate. α,α- Disubstituted α-amino esters with high enantiomeric purity can also be prepared when α-imino esters are the starting substrates.
Novel enantioselective synthesis of both enantiomers of furan-2-yl amines and amino acids
Demir, Ayhan S.,Sesenoglu, Oezge,Uelkue, Dincer,Arici, Cengiz
, p. 91 - 105 (2007/10/03)
A new enantioselective synthesis of furan-2-yl amines and amino acids is described, in which the key step is the oxazaborolidine-catalyzed enantioselective reduction of O-benzyl (E)- and (Z)-furan-2-yl ketone oximes to the corresponding chiral amines. The chirality of the furan-2-yl amines is fully controlled by the appropriate choice of the geometrical isomer of the O-benzyl oxime. Oxidation of the furan ring furnished amino acids in high yields.
A new asymmetric synthesis of (S)-dolaphenine and its heteroaromatic congeners utilizing (+)-2-hydroxy-3-pinanone and (-)-3-hydroxy-2-caranone as chiral auxiliaries
Irako, Naoko,Hamada, Yasumasa,Shioiri, Takayuki
, p. 12731 - 12744 (2007/10/02)
(+)-2-hydroxy-3-pinanone ((+)-HyPN,(+)-2a) and (-)-3-hydroxy-2-caranone ((-)-2b) were respectively converted to the corresponding Schiff bases 18a and 18b with 1-(2-thiazolyl)methylamine (17). Alkylation followed by removal of the chiral auxiliaries (+)-2a and (-)-2b afforded (S)-dolaphenine (10) as an optically pure form. The method was applied to the asymmetric synthesis of the dolaphenine analogs 27a-d.
Asymmetric synthesis. XVIII. Stereocontrolled synthesis of α-substituted-2-furfurylamines via chiral intermediates
Shikui,Aiqiao,Lanjun,Yaozhong
, p. 2485 - 2488 (2007/10/02)
The stereocontrolled synthesis of (R)-α-alkyl-2-furfurylamines (5), using (-)-2-hydroxypinan-3-one as a chiral auxiliary, had been studied. The e.e. values of (5) were 91.4->98%, which determined by capillary GC (stationary phase: Chirasil-Val).
Asymmetric Synthesis XI: Stereoselective Synthesis of α-Alkyl-2-furfurylamines via d-Camphor Ketimine Intermediate
Yaozhong, Jiang,Jingen, Deng,Wenhao, Hu,Giulan, Liu,Aiqiao, Mi
, p. 3077 - 3083 (2007/10/02)
(R)-α-alkyl-2-furfurylamines (7), ranging from 5-67percentd.e., are obtained by asymmetric alkylation of d-camphor ketimine (3).Using 1,3-diiodopropane and dibromoxylene as alkylating reagents, diimine derivatives (6f) and (6g) are formed.However, 1,2-dibromoethane gives coupling product (6h).
