Tetrahedron letters

Carbonyl transposition of α-hydroxyamidals mediated by triphenylphosphine-iodine. A new entry to tetrahydroisoquinolin-4-ones

VL Ponzo, DA Bianchi, TS Kaufman

Index: Ponzo, Viviana L.; Bianchi, Dario A.; Kaufman, Teodoro S. Tetrahedron Letters, 1998 , vol. 39, # 21 p. 3409 - 3412

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Citation Number: 3

Abstract

In a typical procedure, to a stirred solution of the α-hydroxyamidal (0.6 mmol) in dry benzene (3 mL) were successively added PPh 3 (2 equiv.) and a freshly prepared solution of I 2 in benzene (0.5 equiv.). The characteristic colour of the halogen faded rapidly and the reaction mixture was stirred at room temperature until complete disappearance of the starting material was assessed by TLC (0.5 – 2 h). The solvent was removed under reduced pressure and the remaining ...