Kirmse–Doyle‐ and Stevens‐Type Rearrangements of Glutarate‐Derived Oxonium Ylides
Loading...
Access rights
openAccess
acceptedVersion
URL
Journal Title
Journal ISSN
Volume Title
A1 Alkuperäisartikkeli tieteellisessä aikakauslehdessä
This publication is imported from Aalto University research portal.
View publication in the Research portal (opens in new window)
View/Open full text file from the Research portal (opens in new window)
View publication in the Research portal (opens in new window)
View/Open full text file from the Research portal (opens in new window)
Date
Major/Subject
Mcode
Degree programme
Language
en
Pages
9
Series
Chemistry: A European Journal, Volume 24, issue 13, pp. 3209-3217
Abstract
A novel chemoenzymatic synthetic cascade enables the preparation of densely decorated tetrahydrofuran building blocks. Here, the lipase‐catalyzed desymmetrization of 3‐alkoxyglutarates renders highly enantioenriched carboxylic acid intermediates, whose subsequent activation and oxonium ylide rearrangement by means of rhodium or copper complexes furnishes functionalized O‐heterocycles with excellent diastereoselectivity. The two‐step protocol offers a streamlined and flexible synthesis of tetrahydrofuranones bearing different benzylic, allylic or allenylic side chains with full control over multiple stereogenic centers.Description
Other note
Citation
Skrobo, B, Neudörfl, J-M, Schlörer, N E & Deska, J 2018, 'Kirmse–Doyle‐ and Stevens‐Type Rearrangements of Glutarate‐Derived Oxonium Ylides', Chemistry: A European Journal, vol. 24, no. 13, pp. 3209-3217. https://doi.org/10.1002/chem.201704624