Liebigs Annalen der Chemie, 1994-09, Vol.1994 (9), p.931-942
1994
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- Autor(en) / Beteiligte
- Titel
- Stereoselective Amidoalkylation Reactions via N,O-Acetals
- Ist Teil von
- Liebigs Annalen der Chemie, 1994-09, Vol.1994 (9), p.931-942
- Ort / Verlag
- Weinheim: WILEY-VCH Verlag
- Erscheinungsjahr
- 1994
- Quelle
- Wiley Online Library Journals Frontfile Complete
- Beschreibungen/Notizen
- The isomerization of N,O‐acetals 1 yields N‐acyl‐O‐vinyl acetals 2 or 2‐aminomethyl‐1,3‐butadienes 10, depending on the nature of the nitrogen substituents. In the presence of trimethylsilyl trifluoromethanesulfonate (TMSOTf) the N,O‐acetals 2h–u are converted stereoselectively into β‐(N‐acylamino)aldehydes 3. The relative configurations of the products 3 have been determined by X‐ray analysis and 1H‐NMR experiments. The mechanism of the reaction is discussed. Crossover experiments indicate an intermolecular course of the rearrangement.
- Sprache
- Englisch
- Identifikatoren
- ISSN: 0170-2041eISSN: 1099-0690DOI: 10.1002/jlac.199419940915Titel-ID: cdi_crossref_primary_10_1002_jlac_199419940915
- Format
- –
- Schlagworte
- 2-Aminomethyl-1, 2‐Aminomethyl‐1,3‐butadienes, 3-butadienes, Aliphatic compounds, Aliphatic, non-condensed and condensed benzenic, and alicyclic compounds, Amidoalkylation, Amidoalkylation, stereoselective, Chemistry, Condensed matter: structure, mechanical and thermal properties, Exact sciences and technology, Isomerization, N,O‐Acetals, O-Acetals, Organic chemistry, Organic compounds, Physics, Preparations and properties, stereoselective, Structure of solids and liquids, crystallography, Structure of specific crystalline solids, β-(N-Acylamino)aldehydes