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Readily available alkenylboronic acids serve as alkenylation reagents, leading to densely functionalized pyrrolines. Both (<jats:italic>E<\/jats:italic>)\u2010 and (<jats:italic>Z<\/jats:italic>)\u2010cinnamylpyrrolines are accessible depending on the reaction solvent. In dichloromethane, (<jats:italic>E<\/jats:italic>)\u2010cinnamylpyrrolines are produced through a photoredox\u2010mediated single\u2010electron\u2010transfer process. In tetrahydrofuran, (<jats:italic>Z<\/jats:italic>)\u2010cinnamylpyrrolines are generated by photocatalytic contra\u2010thermodynamic <jats:italic>E<\/jats:italic>\u2010to\u2010<jats:italic>Z<\/jats:italic> isomerization of (<jats:italic>E<\/jats:italic>)\u2010cinnamylpyrrolines though an energy\u2010transfer pathway. Two stereocenters are established with complete diastereoselectivity and only one diastereomer is isolated.<\/jats:p>","DOI":"10.1002\/anie.202016941","type":"journal-article","created":{"date-parts":[[2021,2,6]],"date-time":"2021-02-06T11:30:07Z","timestamp":1612611007000},"page":"9672-9679","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":82,"title":["Diastereoselective and Stereodivergent Synthesis of 2\u2010Cinnamylpyrrolines Enabled by Photoredox\u2010Catalyzed Iminoalkenylation of Alkenes"],"prefix":"10.1002","volume":"60","author":[{"given":"Xu","family":"Shen","sequence":"first","affiliation":[{"name":"State Key Laboratory of Analytical Chemistry for Life Science Jiangsu Key Laboratory of Advanced Organic Materials Chemistry and Biomedicine Innovation Center (ChemBIC) School of Chemistry and Chemical Engineering Nanjing University  Nanjing 210023 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