188909-48-0Relevant articles and documents
Stereoselective synthesis of α-substituted serines from protected erythrulose oximes
Carda,Murga,Rodriguez,Gonzalez,Castillo,Marco
, p. 1703 - 1712 (2007/10/03)
The additions of organolithium reagents to the C=N bond of several chiral oxime ethers derived from erythrulose afforded protected amino polyols with high diastereoselectivity. Four of the latter compounds have been convened into the α,α-disubstituted α-amino acids (R)-2-(-)-methylserine, (S)-2-(+)-methylserine, (R)-(+)-2-phenylserine and (R)-(-)-2-n-butylserine.
Diastereoselective additions of organolithium reagents to the C=N bond of protected erythrulose oxime ethers. Synthesis of enantiopure α,α-disubstituted α-aminoacids
Marco, J. Alberto,Carda, Miguel,Murga, Juan,Gonzalez, Florenci,Falomir, Eva
, p. 1841 - 1844 (2007/10/03)
The addition of organolithium reagents to the C=N bond of several erythrulose-derived chiral (E)- and (Z)-ketoxime ethers has been shown to be highly diastereoselective for the (E)-isomers. A chelated transition state has been proposed to explain this result. The addition products were converted into the two α,α-disubstituted α-aminoacids (R)-2-(-)-methylserine and (R)-(+)-2-phenylserine.