27771-05-7Relevant academic research and scientific papers
First asymmetric synthesis of an acyclic β,β-dialkylated-γ-aminobutyric acid
Aguirre, Daniel,Cativiela, Carlos,Díaz-de-Villegas, María D.,Gálvez, José A.
, p. 8142 - 8146 (2007/10/03)
Enantiomerically pure (R)-γ-amino-β-benzyl-β-methylbutyric acid, an acyclic β,β-dialkyl GABA derivative, is efficiently synthesised from (1S,2R,4R)-10-dicyclohexylsulfamoylisobornyl 2-cyanopropanoate by a sequence based on benzylation, Arndt-Eistert homol
Enantioselective biotransformation of α,α-disubstituted dinitriles to the corresponding 2-cyanoacetamides using Rhodococcus sp. CGMCC 0497
Wu, Zhong-Liu,Li, Zu-Yi
, p. 2133 - 2142 (2007/10/03)
A new application of nitrile-converting enzymes in the synthesis of optically active α,α-disubstituted-α-cyanoacetamides from α,α-disubstituted-malononitriles with whole cells of Rhodococcus sp. CGMCC 0497 is described. The products were obtained with enantiomeric excesses of up to >99%, and yields of up to 53%. They are very useful chiral intermediates especially for the synthesis of chiral α,α-disubstituted amino acids but have never been synthesized directly by chemical or enzymatic methods.
Practical synthesis of optically active α,α-disubstituted malonamic acids through asymmetric hydrolysis of malonamide derivatives with Rhodococcus sp. CGMCC 0497
Wu, Zhong-Liu,Li, Zu-Yi
, p. 2479 - 2482 (2007/10/03)
A variety of α,α-disubstituted malonamides undergo enantioselective hydrolysis with Rhodococcus sp. CGMCC 0497 to give challenging enantiopure α,α-disubstituted malonamic acids with up to >99% enantiomeric excesses and 98% chemical yields. The enantiosele
Efficient resolution of rac-2-cyano-2-methyl-3-phenylpropanoic acid. An appropriate starting material for the enantioconvergent synthesis of (S)-α-methylphenylalanine on a large laboratory scale
Badorrey, Ramon,Cativiela, Carlos,Diaz-de-Villegas, Maria D.,Galvez, Jose A.
, p. 2201 - 2207 (2007/10/03)
A large laboratory scale synthesis of (S)-α-methylphenylalanine from benzaldehyde and methyl cyanoacetate has been developed. The synthesis is based on the following sequence: (i) preparation of racemic 2-cyano-2-methyl-3-phenylpropanoic acid, (ii) resolu
Highly enantioselective synthesis of α,α-disubstituted malonamic acids through asymmetric hydrolysis of dinitriles with Rhodococcus sp. CGMCC 0497
Wu, Zhong-Liu,Li, Zu-Yi
, p. 386 - 387 (2007/10/03)
Highly enantioselective hydrolysis of α,α-disubstituted malononitriles by the strain Rhodococcus sp. CGMCC 0497 expressing both nitrile hydratase and amidase activity to give (R)-α,α-disubstituted malonamic acids which could be converted to valuable (R)-
New approaches to the asymmetric synthesis of α-methylphenylalanine
Cativiela,Diaz-de-Villegas,Galvez
, p. 261 - 268 (2007/10/02)
A strategy of highly selective alkylation of chiral 2-cyanoesters followed by the corresponding degradation process allows a divergent asymmetric synthesis of (R) and (S)-α-methylphenylalanine.
Chiral 2-Cyanocinnamates in Conjugate Addition Asymmetric Enolate Trapping Reactions
Cativiela, Carlos,Diaz-de-Villegas, Maria Dolores,Galvez, Jose Antonio
, p. 1657 - 1661 (2007/10/02)
Chiral 2-cyannocinnamates react with L-selectride to give an intermediate enolate which can be stereoselectively trapped with different halides to afford α-substituted phenylalanine precursors with excellent chemical yields and good diastereomeric excess.
ASYMMETRIC DIALKYLATION OF α-CYANOACETIC ACID
Hanamoto, Takeshi,Katsuki, Tsutomu,Yamaguchi, Masaru
, p. 2463 - 2464 (2007/10/02)
Formation of the quarternary asymmetric center by double alkylation of cyanoacetamide enolate bearing trans-2,5-bis(methoxymethoxymethyl)pyrrolidine moiety as a chiral auxiliary, was carried out with high diastereoselectivity.
