Evidence for alternative mechanisms in the amino-Cope rearrangement
β Scribed by Steven M. Allin; Martin A.C. Button
- Book ID
- 104261315
- Publisher
- Elsevier Science
- Year
- 1999
- Tongue
- French
- Weight
- 95 KB
- Volume
- 40
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
The formal amino-Cope rearrangement of a 3-amino-l,5-diene substrate does not proceed solely by a concerted [3,3]-sigmatropic rearrangement mechanism.
π SIMILAR VOLUMES
There is evidence that Cope Rearrangements may occur by as many as four distinct mechanisms, of which only one is the usual concerted mechanism (1). In 1972, Goldstein and Benzon reported the discovery of a second degenerate rearrangement of 1,5-hexadiene, occurring only at high temperature (250-300
The anionic amino-Cope rearrangement of suitably functionalized acyclic 3-amino-l,5-dicnΒ’ substrates has been achieved and we report the first example of an asymmetric anionic amino-Cope rearrangement to yield an enantiomerically enriched product (75% e.e.). The absolute stereochemisU3, of the produ
The First Example of Asymmetric Induction in an Anionic Amino-Cope Rearrangement. -In continuation of a previous work, the preliminary investigations on the anionic variant of the amino-Cope rearrangement are presented, including the title asymmetric example (R)-(VIII). Starting from the correspond