Asymmetric synthesis of 3-substituted dihydro-2H-isoquinolin-1-ones, dihydro- and tetrahydroisoquinolines via 1,2-addition/ring closure
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 N-N bond cleavage to remove the auxiliary. Moderate to good yields and high enantiomeric excesses (ee = 85-99%) are reached.
Enders, Dieter,Braig, Volker,Boudou, Marine,Raabe, Gerhard
p. 2980 - 2990
(2007/10/03)
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