Article ; Online: An Organocatalytic Oxy-Cope/Michael Cascade Reaction.
Organic letters
2023 Volume 25, Issue 5, Page(s) 777–781
Abstract: ... an intramolecular Michael reaction to furnish cyclopentane-containing products. The reaction proceeds with a range ...
Abstract | Ethyl diazepane carboxylate catalyzes the oxy-Cope rearrangement of 4-hydroxy- and 4-alkoxy-1,5-hexadiene-2-carboxaldehydes via iminium ion activation. The resulting intermediate undergoes an intramolecular Michael reaction to furnish cyclopentane-containing products. The reaction proceeds with a range of substrates, including both cyclic and acyclic substrates, and tolerates substitution on the vinyl substituent. Substrates fused on a cycloalkane framework undergo net ring expansion/cyclopentannulation with a high degree of stereocontrol via chairlike transition states. The reaction extends iminium organocatalysis to the oxy-Cope rearrangement, embedded within a complexity-generating cascade transformation. |
---|---|
Language | English |
Publishing date | 2023-01-26 |
Publishing country | United States |
Document type | Journal Article |
ISSN | 1523-7052 |
ISSN (online) | 1523-7052 |
DOI | 10.1021/acs.orglett.2c04269 |
Database | MEDical Literature Analysis and Retrieval System OnLINE |
More links
Kategorien
Order via subito
This service is chargeable due to the Delivery terms set by subito. Orders including an article and supplementary material will be classified as separate orders. In these cases, fees will be demanded for each order.
Inter-library loan at ZB MED
Your chosen title can be delivered directly to ZB MED Cologne location if you are registered as a user at ZB MED Cologne.