Abstract
Depending on the keto-enol equilibrium 1 ⇄ 2 reduction of the esters and the amides 1/2 a—g with Zn(BH4)2/ZnCl2 attacks either at the CO or at the CO2R group. A high diastereoselectivity (98:2 or more) is observed for the formation of the β-hydroxy compounds 3a,b,c,e,f in favour of the erythro forms. As to the structure determination of 3, different steric effects and different intramolecular hydrogen bonding have to be considered, leading to different rotameric populations.
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