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Despite tremendous progress in the synthesis of imidazo[1,5\u2010a]pyridines over the past decade, many of them can still not be efficiently prepared. Herein, we report an anomeric stereoauxiliary approach for the synthesis of a wide range of imidazo[1,5\u2010a]pyridines after cleaving the C\u2212N bond of <jats:sc>d<\/jats:sc>\u2010glucosamine (\u03b1\u20102\u00b0 amine) from biobased resources. This new approach expands the scope of readily accessible imidazo[1,5\u2010a]pyridines relative to existing state\u2010of\u2010the\u2010art methods. A key strategic advantage of this approach is that the \u03b1\u2010anomer of <jats:sc>d<\/jats:sc>\u2010glucosamine enables C\u2212N bond cleavage via a seven\u2010membered ring transition state. By using this novel method, a series of imidazo[1,5\u2010a]pyridine derivatives (&gt;80 examples) was synthesized from pyridine ketones (including <jats:italic>para<\/jats:italic>\u2010dipyridine ketone) and aldehydes (including <jats:italic>para<\/jats:italic>\u2010dialdehyde). Imidazo[1,5\u2010a]pyridine derivatives containing diverse important deuterated C(sp<jats:sup>2<\/jats:sup>)\u2212H and C(sp<jats:sup>3<\/jats:sup>)\u2212H bonds were also efficiently achieved.<\/jats:p>","DOI":"10.1002\/chem.202200648","type":"journal-article","created":{"date-parts":[[2022,3,23]],"date-time":"2022-03-23T06:33:32Z","timestamp":1648017212000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":14,"title":["Anomeric Stereoauxiliary Cleavage of the C\u2212N Bond of <scp>d<\/scp>\u2010Glucosamine for the Preparation of Imidazo[1,5\u2010a]pyridines"],"prefix":"10.1002","volume":"28","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-7901-2738","authenticated-orcid":false,"given":"Kui","family":"Zeng","sequence":"first","affiliation":[{"name":"Sustainable Materials and Chemistry Georg-August-University of G\u00f6ttingen  B\u00fcsgenweg 4 37077 G\u00f6ttingen 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