110936-12-4Relevant articles and documents
Synthesis of optically active (2-arylvinyl)glycine derivatives by palladium-catalyzed arylation of (s)-n-(benzyloxycarbonyl)vinylglycine
Itaya, Taisuke,Hozumi, Yoshitaka
, p. 1094 - 1101 (2007/10/03)
Phenyl, tolyl, anisyl, and 1-naphthyl iodides (7a-g,n) smoothly reacted with (S)-N-(benzyloxycarbonyl)-vinylglycine (6) in H2O in the presence of Pd(OAc)2, Bu4NCI, and NaHCO3 at 45°C, producing [S-(E)]-(2- arylvinyl)glycine derivatives 8a-g, n of high enantiomeric purity. The yields of the reactions of 3- (7f), 2- (7e), and 4-iodoanisoles (7g) increased in this order. This relationship between the yield and the position of substitution has been found to hold for bromophenyl iodides (7i-k), although somewhat lower chemical and optical yields were realized in these cases. Phenyl iodide 71 carrying an electron-withdrawing 4-acetyl group gave an unsatisfactory result, and more electron-deficient 4-nitrophenyl iodide (7m) did not provide the desired product. All these results suggest that the reaction is advantageous with electron-sufficient substrates 7. However, this was not the case for 4-iodophenol (7h), as well as some heterocyclic iodides.
Practical Enantioselective Synthesis of a Homotyrosine Derivative and (R,R)-4-Propyl-9-hydroxynaphthoxazine, a Potent Dopamine Agonist
Melillo, David G.,Larsen, Robert D.,Mathre, David J.,Shukis, William F.,Wood, Alfred W.,Colleluori, Joseph R.
, p. 5143 - 5150 (2007/10/02)
Two enantioselective routes were developed to prepare chiral amino acid derivative 4.The key step in the first route was catalytic hydrogenation of acrylate derivative 3 using chiral rhodium catalysts.In the second route the key step was acylation of 2-ch
