Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 61, Issue 11, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202113925
Keywords
Asymmetric Synthesis; Cyclopropanation; Cyclopropanol; Epoxidation; Rubottom Oxidation
Categories
Funding
- European Research Council (ERC Consolidator Grant SeleCHEM) [771170]
- EPFL
- Swiss National Science Foundation
- Ecole Polytechnique Federale de Lausanne
- European Research Council (ERC) [771170] Funding Source: European Research Council (ERC)
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The paper explores the enantioselective diversification of a single starting material by extending the concept of catalytically formed chiral auxiliary from hydrogenation to cyclopropanation and epoxidation reactions. This approach eliminates the need for different chiral catalysts in alkene functionalization and allows for the control of stereochemistry using a catalytically constructed chiral auxiliary.
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 alpha-amino-alpha-hydroxy ketones.
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