2-amino-1-phenyl-propan-1,3-diol as chiral auxiliary. Application in the synthesis of cis 3-phthalimido-4-styryl-2-azetidinones

Article abstract of DOI:10.1016/S0040-4020(97)00483-3

3,4-cis3,4-cis-1-N-(1'-phenyl-1',3'-dihydroxy-2'-propyl)-3-phthalimido-4 -styrylazetidinones were obtained in optically pure form by chiral Staudinger reaction. The cis-α/β-ratio could be influenced by the protective groups of the diol moiety. Removal of the chiral auxiliarity could be accomplished by direct oxidation, or by previous double bond formation, thus the 2-amino-1-phenyl-propan-1,3-diol can be regarded to a generally useful chiral auxiliary.