Abstract
The diastereospecific formation of β-N-glycosidically linked α,β-unsaturated δ-aminocarbonyl
derivatives, in the form of (S )-δ-amino-δ-arylpent-2-enoic
ester, has been achieved in high yield via a vinylogous Mannich
reaction, utilizing poly-O-pivaloylated d -galacosylamine
as the chiral auxiliary. (S )-6-p -Tolylpiperidine-2-one can be stereoselectively
synthesized from (S )-δ-amino-δ-arylpent-2-enoic
ester by sequential hydrogenation of the double bond, cyclic lactam
formation, and removal of the N-glycosidic auxiliary under basic
conditions.
Key words
vinylogous Mannich reaction - carbohydrate - chiral auxiliary - stereoselective synthesis - 6-arylpiperidin-2-ones
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