Distinction of Diastereofaces at the α-Position of Chiral Cyclic Acetals

Article abstract of DOI:10.1016/S0957-4166(00)86042-5

Key words: chiral acetal; asymmetric 1,2-addition; asymmetric 1,4-addition; C2 symmetry; determination of optical purity; chiral carboxylic acid Asymmetric 1,2- and 1,4-additions to substrates with an acetal as a chiral auxiliary have been studied.Among the tested substrates, C2-symmetrical 5c was most effective for 1,2-addition with MeTi(O-iPr)3.Furthermore, C2-symmetrical carbinol 5b has been found to be a potent 1H-NMR reagent for determination of optical purity of carboxylic acids with a chiral center at the α-position.