Asymmetric Cyclopropanation and Epoxidation via a Catalytically Formed Chiral Auxiliary

Abstract: For the enantioselective diversification of a single starting material, a different chiral catalyst is usually required for each transformation. Herein, we extend the concept of catalytically formed chiral auxiliary from hydrogenation to the asymmetric cyclopropanation and epoxidation of tetra‐substituted olefins, alleviating the need for different chiral catalysts in the alkene functionalization step. The chiral auxiliary is catalytically constructed from propargylic amines in a Pd‐catalyzed enantioselective carboetherification step using a commercially available trifluoroacetaldehyde hemiacetal tether. The installed auxiliary is then controlling the stereochemistry of the cyclopropanation and the epoxidation using standard highly reactive reagents to give enantioenriched spirocyclic aminomethylcyclopropanols and α‐amino‐α‐hydroxy ketones.

Object Details

• Location: Deutsche Nationalbibliothek Frankfurt am Main
• Extent: Online-Ressource
• Language: Englisch

References and Relationships

• Bibliographic citation: Asymmetric Cyclopropanation and Epoxidation via a Catalytically Formed Chiral Auxiliary ; day:01 ; month:02 ; year:2022 ; extent:1 ; Angewandte Chemie ; (01.02.2022) (gesamt 1)

Contributors, Places and Time

• Creator: Puriņš, Mikus ; Waser, Jerome

Further information

• DOI: 10.1002/ange.202113925
• URN: urn:nbn:de:101:1-2022020114410669253449
• Rights: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
• Last update: 15.08.2025, 7:32 AM CEST