Synthesis

Asymmetric synthesis of 3-substituted dihydro-2H-isoquinolin-1-ones, dihydro-and tetrahydroisoquinolines via 1, 2-addition/ring closure

D Enders, V Braig, M Boudou, G Raabe

Index: Enders, Dieter; Braig, Volker; Boudou, Marine; Raabe, Gerhard Synthesis, 2004 , # 18 p. 2980 - 2990

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Citation Number: 13

Abstract

Abstract The asymmetric synthesis of 3-substituted dihydro-2H-isoquinolin-1-ones, dihydro- and tetrahydroisoquinolines is described. The key operation is a tandem 1, 2-addition/ring closure sequence employing lithiated ortho-toluamides and aldehyde SAMP-or RAMP- hydrazones as substrates, followed by NN bond cleavage to remove the auxiliary. Moderate to good yields and high enantiomeric excesses (ee= 85-99%) are reached.