The First Chiral Version of Jackson N-Benzyl-N- Tosylaminoacetal Cyclization - A New Enantioselective Total Synthesis of 1-S-(-)-Salsolidine

PONZO, VL; KAUFMAN, TS

TETRAHEDRON LETTERS

Elsevier

Lugar: Amsterdam; Año: 1995 vol. 36 p. 9105 - 9108

The First chiral versión of of Jackson N-benzyl-N-tosylamidoacetal cyclization, is reported, enabling a new and efficient enantioselective total synthesis of salsolidine. Chirality was introduced by oxazaborolidine  catalized reduction of an aralkyl ketone, coupled to a Mitsunobu-type amination of the resulting benzylic alcohol, furnishing a complete configurational inversion of the latter.