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Although many biochemical reactions involve imine formation, the inherently unstable property of <jats:italic>N<\/jats:italic>\u2010alkyl\u2010\u03b1,\u03b2\u2010unsaturated imines still hindered their utilization in organic synthesis. In this article, we described that the <jats:italic>N<\/jats:italic>\u2010alkyl\u2010\u03b1,\u03b2\u2010unsaturated imines, which prepared from alkylamines and acrolein, could smoothly react through [4 + 4] cycloaddition to give eight\u2010membered diazacyclooctane derivatives in excellent yields. Under a similar condition, in the presence of formaldehyde, the [4 + 2] and [4 + 2 + 2] cycloadditions could lead to the formation of six\u2010membered hexahydropyrimidine or eight\u2010membered triazacyclooctanes, depending on the substituent of aldehydes. Moreover, an easy functional group manipulation of the cyclic products obtained from these cycloadditions can provide variously substituted chiral linear diamines. We can utilize these novel reactivities to reveal the unknown and essential properties of many biological processes that involve <jats:italic>N<\/jats:italic>\u2010alkyl\u2010unsaturated imines.<\/jats:p>","DOI":"10.1002\/chir.23265","type":"journal-article","created":{"date-parts":[[2020,7,4]],"date-time":"2020-07-04T00:35:28Z","timestamp":1593822928000},"page":"1160-1168","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":5,"title":["Enantioselective synthesis of cyclic and linear diamines by imine cycloadditions"],"prefix":"10.1002","volume":"32","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-8445-2810","authenticated-orcid":false,"given":"Tsung\u2010Che","family":"Chang","sequence":"first","affiliation":[{"name":"Biofunctional Synthetic Chemistry Laboratory RIKEN Cluster for Pioneering Research  Saitama 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