The first chiral version of Jackson N-benzyl-N-tosylaminoacetal cyclization. A new enantioselective total synthesis of 1-S-(-)-salsolidine

Article abstract of DOI:10.1016/0040-4039(95)01975-N

The first chiral version of Jackson N-benzyl-N-tosylaminoacetal cyclization, enabling a new and efficient enantioselective total synthesis of 1-S-(-)-salsolidine, is reported. Chirality was introduced by oxazaborolidine-catalyzed reduction of an aralkyl ketone, coupled with a Mitsunobu-type amination of the resulting benzylic alcohol, resulting in complete configurational inversion of the latter.