2-AMINO-1-PHENYL-PROPAN-1,3-DIOL AS CHIRAL AUXILIARY - APPLICATION INTHE SYNTHESIS OF CIS 3-PHTHALIMIDO-4-STYRYL-2-AZETIDINONES

,4-cis-1-N-(1'-phenyl-1',3'-dihydroxy-2'-propyl)-3 -phthalimido-4-styr ylazetidinones were obtained in optically pure form by chiral Stauding er reaction. The cis-alpha/beta-ratio could be influenced by: the prot ective groups of the diol moiety. Removal of the chiral auxiliarity co uld be accomplished by direct oxidation, or by previous double bond fo rmation, thus the 2-amino-1-phenyl-propan-1,3-diol can be regarded to a generally useful chiral auxiliary. (C) 1997 Elsevier Science Ltd.