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Herein, we extend the concept of catalytically formed chiral auxiliary from hydrogenation to the asymmetric cyclopropanation and epoxidation of tetra\u2010substituted 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\u2010catalyzed 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 \u03b1\u2010amino\u2010\u03b1\u2010hydroxy ketones.<\/jats:p>","DOI":"10.1002\/anie.202113925","type":"journal-article","created":{"date-parts":[[2022,1,14]],"date-time":"2022-01-14T09:44:23Z","timestamp":1642153463000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":14,"title":["Asymmetric Cyclopropanation and Epoxidation via a Catalytically Formed Chiral Auxiliary"],"prefix":"10.1002","volume":"61","author":[{"given":"Mikus","family":"Puri\u0146\u0161","sequence":"first","affiliation":[{"name":"Laboratory of Catalysis and Organic Synthesis and NCCR Catalysis Institut des Sciences et Ing\u00e9nierie Chimique Ecole Polytechnique F\u00e9d\u00e9rale de Lausanne  1015 Lausanne Switzerland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4570-914X","authenticated-orcid":false,"given":"Jerome","family":"Waser","sequence":"additional","affiliation":[{"name":"Laboratory of Catalysis and Organic Synthesis and NCCR Catalysis Institut des Sciences et Ing\u00e9nierie Chimique Ecole Polytechnique F\u00e9d\u00e9rale de Lausanne  1015 Lausanne Switzerland"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2022,2]]},"reference":[{"key":"e_1_2_2_1_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.5b00676"},{"key":"e_1_2_2_2_1","doi-asserted-by":"publisher","DOI":"10.1126\/science.1083622"},{"key":"e_1_2_2_3_1","doi-asserted-by":"publisher","DOI":"10.1002\/9783527635207"},{"key":"e_1_2_2_4_1","unstructured":"G. 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