TY - JOUR
T1 - Asymmetric synthesis of quaternary α-amino acids using D-ribonolactone acetonide as chiral auxiliary
AU - Moreno-Mañas, M.
AU - Trepat, E.
AU - Sebastián, R.M.
AU - Vallribera, A.
PY - 1999/10/1
Y1 - 1999/10/1
N2 - We describe a new simple methodology to prepare enantiopure α,α- dialkylglycines based on the use of commercially available D-ribonolactone as a chiral auxiliary. Enantiopure α-methyl and α-butyl series are prepared through diastereoselective alkylation and subsequent Schmidt rearrangement of α,α-dialkylacetoacetates of D-ribonolactone acetonide. Absolute configuration was assigned through preparation of enantiopure 4,4- disubstituted 3-methyl-2-pyrazolin-5-ones.
AB - We describe a new simple methodology to prepare enantiopure α,α- dialkylglycines based on the use of commercially available D-ribonolactone as a chiral auxiliary. Enantiopure α-methyl and α-butyl series are prepared through diastereoselective alkylation and subsequent Schmidt rearrangement of α,α-dialkylacetoacetates of D-ribonolactone acetonide. Absolute configuration was assigned through preparation of enantiopure 4,4- disubstituted 3-methyl-2-pyrazolin-5-ones.
U2 - 10.1016/S0957-4166(99)00457-7
DO - 10.1016/S0957-4166(99)00457-7
M3 - Article
SN - 0957-4166
VL - 10
SP - 41
EP - 49
JO - Tetrahedron Asymmetry
JF - Tetrahedron Asymmetry
ER -