| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1390286 | Carbohydrate Research | 2013 | 7 Pages |
•The diastereospecific formation of β-N-glycosidically linked α,β-unsaturated δ-amino aldehyde derivatives has been achieved with high yield via a vinylogous Mannich reaction.•The reaction was performed by using a O-pivaloylated galactosyl amine as a chiral template and AlCl3 as a promoter in THF.•(S)-8-(p-Nitrophenyl) azocan-2-one can be stereoselective synthesized under mild condition.
The diastereospecific formation of β-N-glycosidically linked α,β-unsaturated δ-amino aldehyde derivatives has been achieved with high yield via a vinylogous Mannich reaction. The reaction was performed by using a O-pivaloylated galactosyl amine as a chiral template and AlCl3 as a promoter in THF. (S)-8-(p-Nitrophenyl) azocan-2-one can be stereoselective synthesized from (S) ethyl 7-galactosylamino-7-(p-nitrophenyl)hepta-2,4-dienoate by sequential hydrogenation of the double bond, cyclic lactam formation, and removal of the N-glycosidic auxiliary under basic conditions.
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