ORCID: https://orcid.org/0000-0003-0009-8629
(2020):
Traceless Isoprenylation of Aldehydes via N‐Boc‐N‐(1,1‐dimethylallyl)hydrazones.
In: European Journal of Organic Chemistry, Vol. 2020, No. 24: pp. 3680-3687
[PDF, 1MB]
Abstract
A short isoprenylation protocol starting from non‐conjugated N‐Boc‐N‐(1,1‐dimethylallyl)hydrazones was developed utilising Thomson's traceless bond construction. This type of [3,3]‐sigmatropic rearrangement is catalysed by the Brønsted acid triflimide and liberates only gaseous by‐products. The required N‐Boc‐N‐allylhydrazine precursor is available in three steps starting from a known diazene using biocatalytic aldol addition and Tebbe olefination as key steps. Allylhydrazones are prepared via condensation with appropriate aldehydes. Scope and limitations of the [3,3]‐sigmatropic rearrangements are analysed.
| Item Type: | Journal article |
|---|---|
| Faculties: | Chemistry and Pharmacy > Department of Pharmacy |
| Subjects: | 500 Science > 540 Chemistry 600 Technology > 610 Medicine and health |
| URN: | urn:nbn:de:bvb:19-epub-73513-9 |
| ISSN: | 1099-0690 |
| Language: | English |
| Item ID: | 73513 |
| Date Deposited: | 29. Sep 2020 13:15 |
| Last Modified: | 04. Nov 2020 13:53 |
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