The development of a novel carbamate linker optimized for solid phase N-acyliminium ion chemistry is reported. Some 2-and 2,4-substituted pyrrolidines were synthesized via addition of several carbon nucleophiles to immobilized N-acyliminium ions. A ~-sulfonylethyl carbamate linker appeared especiall
Synthesis of homoallylic amines via N-acyliminium ion reactions on solid support
โ Scribed by Wim J.N. Meester; Floris P.J.T. Rutjes; Pedro H.H. Hermkens; Henk Hiemstra
- Publisher
- Elsevier Science
- Year
- 1999
- Tongue
- French
- Weight
- 222 KB
- Volume
- 40
- Category
- Article
- ISSN
- 0040-4039
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โฆ Synopsis
The synthesis of a library of homoallylic amines is reported. The key step in the synthesis is a one-pot Nacyliminium ion coupling involving a solid phase-bound carbamate, an aldehyde and an allylsilane under Lewis acid conditions.
๐ SIMILAR VOLUMES
A total synthesis of racemic a-allokainic acid is described, which starts from allylsilane 8 and methoxy-or chloroglycine derivative 9, and proceeds fully stereoselectively in nine steps and 1.1% overall yield. Key steps are the intermolecular N-acyliminium ion coupling of 8 with 9 and an intramolec
Epoxides were synthesized on a solid support via an immobilized sulfonium salt, which is generated from a bromoacetic amide. Subsequent ring opening with amines leads to a single diastereoisomer of an amino alcohol, which can be cleaved from the solid support.