Tetrahedron p. 1895 - 1910 (1991)
Update date:2022-07-30
Topics:
Wanner, Klaus Th.
Hoefner, Georg
The reduction of the amidoketones (R)-1 and (S)-2 has been achieved in a stereocontrolled manner giving either the product with like- or unlike configuration depending upon the reducing agent employed. Thus with Li(OtBu)3AlH the amidoalcohols (R,R)-3 and (S,S)-5 were the major diastereomers formed whereas with K(sBu)3BH (R,S)-4 and (S,R)-6 dominated. Stereoselectivities up to 98/2 were observed. As a mechanistic rationale for the change of direction in the asymmetric induction a chelate-and non-chelate-model have been envoked. By including (rac)-9 in this study having a non chiral acyl group it was found that the chiral auxiliary in.
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