848829-67-4Relevant academic research and scientific papers
Stereoselective synthesis of 4-hydroxy-2-phenylproline framework
Maeda, Kenji,Miller, Ross A.,Szumigala Jr., Ronald H.,Shafiee, Ali,Karady, Sandor,Armstrong III, Joseph D.
, p. 1545 - 1549 (2005)
Highly diastereoselective (>20:1) bromo-lactonization of N-sulfonyl-2-allyl-2-phenylglycine methyl ester (11) was observed. Successive treatment of the chiral lactone with MeONa gave the desired (2S,4R)-4-hydroxy-2- phenylproline derivative in high yield without erosion of the diastereoselectivity. The starting chiral non-racemic compound (5) was prepared from the racemic 2-phenylglycine using a classical kinetic resolution (crystallization), an asymmetric phase transfer alkylation, and an enzyme-catalyzed kinetic resolution.
