Synthesis of ketones and aldehydes via reactions of Weinreb-type amides on solid support
โ Scribed by Tam Q Dinh; Robert W Armstrong
- Publisher
- Elsevier Science
- Year
- 1996
- Tongue
- French
- Weight
- 193 KB
- Volume
- 37
- Category
- Article
- ISSN
- 0040-4039
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๐ SIMILAR VOLUMES
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.
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.
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.