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Although the reaction is inherentely stereoselective in cyclic systems, the results achieved using acylic diketone systems can be less satisfactory. This report describes a highly stereoselective BAR in an acyclic system that gives a glycolic acid product which is then transformed via an elimination reaction to an unusual isoaurone product, in fact this latter product was the key to unravelling the stereochemistry of the glycolic acid product. The elimination reaction mechanism was studied using computational approaches.<\/jats:p>","DOI":"10.1002\/ajoc.202100692","type":"journal-article","created":{"date-parts":[[2022,1,29]],"date-time":"2022-01-29T02:31:42Z","timestamp":1643423502000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":1,"title":["Transformation of a Chiral Glycolic Acid to an Isoaurone: Stereochemical Assignment of a Benzilic Acid Rearrangment Product"],"prefix":"10.1002","volume":"11","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-8248-1116","authenticated-orcid":false,"given":"Anthony J.","family":"Burke","sequence":"first","affiliation":[{"name":"Chemistry Department School of Science and Technology Universidade de \u00c9vora  Rua Rom\u00e3o Romalho 59 7000 \u00c9vora Portugal"},{"name":"LAQV-REQUIMTE Institute for Research and Advanced Studies Universidade de \u00c9vora  Rua Rom\u00e3o Romalho 59 7000 \u00c9vora Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8422-9392","authenticated-orcid":false,"given":"Carla S. 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