1577180-41-6Relevant articles and documents
Stereoselective synthesis of 3,4-dihydroxylated prolines and prolinols starting from L -tartaric acid
Oba,Koguchi,Nishiyama
, p. 237 - 243 (2014/02/14)
A straightforward and stereoselective synthesis of 3,4-dihydroxyprolines and 3,4-dihydroxyprolinols is described. The key reaction in this synthesis is a protective group-controlled diastereoselective cyanation of a chiral acyliminium intermediate derived from l-tartaric acid. Methanolysis of the obtained cyanolactam gave methyl 3,4-dihydroxypyroglutamate that was converted to 3,4-dihydroxyproline and 3,4-dihydroxyprolinol by reduction of the lactam carbonyl and ester groups in a stepwise manner.