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- Title
Diastereoselective Reductive Cyclization of Allene‐Tethered Ketoamines via Copper‐Catalyzed Cascade Carboboronation and Protodeborylation.
- Authors
Ashraf, Muhammad Awais; Tambe, Shrikant D.; Cho, Eun Jin
- Abstract
A copper‐catalyzed cascade process has been developed for the synthesis of 3‐hydroxypyrrolidine derivatives in a highly diastereoselective manner. The reaction proceeded via borylative allyl copper intermediate formation from allenes; the intermediate underwent intramolecular diastereoselective cyclization followed by cascade copper‐catalyzed protodeborylation, to give 3‐hydroxypyrrolidines. This method could be extended to the synthesis of six‐membered piperidine analogs. A series of control experiments were carried out to confirm the Cu‐catalyzed facile protodeborylation of borylated homoallylic alcohols at room temperature.
- Subjects
RING formation (Chemistry); ALLENE; PIPERIDINE; COPPER; CATALYSIS; CYCLOPENTANE
- Publication
Bulletin of the Korean Chemical Society, 2021, Vol 42, Issue 4, p683
- ISSN
0253-2964
- Publication type
Article
- DOI
10.1002/bkcs.12241