THE FIRST CHIRAL VERSION OF JACKSON N-BENZYL-N-TOSYLAMINOACETAL CYCLIZATION - A NEW ENANTIOSELECTIVE TOTAL SYNTHESIS OF 1-S-(-)-SALSOLIDINE

Authors
PONZO VL KAUFMAN TS
Citation
Vl. Ponzo et Ts. Kaufman, THE FIRST CHIRAL VERSION OF JACKSON N-BENZYL-N-TOSYLAMINOACETAL CYCLIZATION - A NEW ENANTIOSELECTIVE TOTAL SYNTHESIS OF 1-S-(-)-SALSOLIDINE, Tetrahedron letters, 36(50), 1995, pp. 9105-9108
Citations number
22
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
36
Issue
50
Year of publication
1995
Pages
9105 - 9108
Database
ISI
SICI code
0040-4039(1995)36:50<9105:TFCVOJ>2.0.ZU;2-Y
Abstract
The first chiral version of Jackson N-benzyl-N-tosylaminoacetal cycliz ation, enabling a new and efficient enantioselective total synthesis o f 1-S-(-)-salsolidine, is reported. Chirality was introduced by oxazab orolidine-catalyzed reduction of an aralkyl ketone, coupled with a Mit sunobu-type amination of the resulting benzylic alcohol, resulting in complete inversion of the latter.