Diastereoselective Reductive Cyclization of Allene-Tethered Ketoamines via Copper-Catalyzed Cascade Carboboronation and Protodeborylation
- Authors
- Ashraf, Muhammad Awais; Tambe, Shrikant D.; Cho, Eun Jin
- Issue Date
- Apr-2021
- Publisher
- WILEY-V C H VERLAG GMBH
- Keywords
- Copper; Cascade catalysis; Allene; 3-Hydroxypyrrolidine; Protodeborylation
- Citation
- BULLETIN OF THE KOREAN CHEMICAL SOCIETY, v.42, no.4, pp 683 - 690
- Pages
- 8
- Journal Title
- BULLETIN OF THE KOREAN CHEMICAL SOCIETY
- Volume
- 42
- Number
- 4
- Start Page
- 683
- End Page
- 690
- URI
- https://scholarworks.bwise.kr/cau/handle/2019.sw.cau/43987
- DOI
- 10.1002/bkcs.12241
- ISSN
- 0253-2964
1229-5949
- 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.
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Collections - College of Natural Sciences > Department of Chemistry > 1. Journal Articles
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