ENANTIOMERE DER 2,2'-DINITROBIPHENYL-6,6'-DICARBONSAEURE ALS STEREOSELEKTIV WIRKSAME, REVERSIBLE SCHUTZGRUPPEN-II. STEREOSELEKTIVE SYNTHESEN VON LIPIDGRUNDKOERPERN ODER -BAUSTEINEN

Article abstract of DOI:10.1016/S0040-4020(01)87373-7

S-(-)-1,1'-diphenyl-2,2'-dinitro-6,6'-dicarboxylic acid (1) is used as an axial-chiral protecting group for the primary hydroxy group of glycerol and glycerol derivatives.Diesters of 1 were formed which have the largest distance between the nitro groups and the nucleophilic substituents on glycerol.After hydrogenolytical removal of the protecting group asymmetric glycerol derivatives were obtained with approximately 10percent enantiomeric excess.Hydroxybromination of 12 resulted mainly in he anti-Markovnikov 13a instead of the Markovnikov product 13b expected, which was present only in traces.This deviation is discussed.