STUDY OF ENANTIOSELECTIVITY OBSERVED IN T HE SYNTHESIS OF ATDP MONOSALTS OF FUNCTIONALIZED 1,3-DIOLS

The synthesis of ATDP monosalts of biprimary 1,3-diols functionalised with one alpha-aminoacid bearing an asymetric carbon, leads to two dia stereoisomers with a ratio of 2:1 the origin of the enantioselectivity has been studied by an experimental approach (temperature and structu ral effects) as well as by a theoretical one (PM3 calculations). A mec hanism explaining the observed enantioselectivity is proposed implicat ing reaction intermediates derived from the theoretical calculations. They show preferential conformations related to intramolecular hydroge n bonding.