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.
Synthesis of amino alcohols on solid support via sulfonium-ion mediated Darzens reaction
โ Scribed by Bernd Peschke; Joan Gredal Bundgaard; Jens Breinholt
- Publisher
- Elsevier Science
- Year
- 2001
- Tongue
- French
- Weight
- 100 KB
- Volume
- 42
- Category
- Article
- ISSN
- 0040-4039
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โฆ Synopsis
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.
๐ SIMILAR VOLUMES
Solid phase intramolecularHeck couplingallows the syothesisof 2-oxindoles. Additional diversityis introducedinfo the moleculeby reductiveatkylationprior to the Heck cyclisationarrdatso by conjugateadditionof a varietyof nucleophilesontothe cyctisedproductprior to cleavage. 01997 Elsevier ScienceLtd.