03513nam a22005175i 4500001001800000003000900018005001700027007001500044008004100059020003700100024003500137050001400172072001600186072002300202072001500225100008300240245010900323250001800432264007200450300006600522336002600588337002600614338003600640347002400676490007200700505036200772520131601134650003102450650001502481650002502496650002502521650003002546650003102576650002502607650002502632710003402657773002602691776003602717776003602753776003602789830007902825856004602904912001402950912001402964999001702978978-981-97-0787-4DE-He21320251030111807.0cr nn 008mamaa240405s2024    si |    s    |||| 0|eng d  a97898197078749978-981-97-0787-47 a10.1007/978-981-97-0787-42doi 4aQD241-441 7aPNN2bicssc 7aSCI0130402bisacsh 7aPNN2thema1 aIto, Tomohiro.eauthor.4aut4http://id.loc.gov/vocabulary/relators/aut97479810aSynthesis of Medium-Sized Cycloalkenes via Fused-Cyclobutenesh[electronic resource] /cby Tomohiro Ito.  a1st ed. 2024. 1aSingapore :bSpringer Nature Singapore :bImprint: Springer,c2024.  aXII, 129 p. 162 illus., 25 illus. in color.bonline resource.  atextbtxt2rdacontent  acomputerbc2rdamedia  aonline resourcebcr2rdacarrier  atext filebPDF2rda1 aSpringer Theses, Recognizing Outstanding Ph.D. Research,x2190-50610 aIntroduction -- Synthesis of Functionalized Medium-Sized trans-Cycloalkenes by 4π Electrocyclic Ring Opening Alkylation Cascade -- Synthesis of γ-Aryl Medium Sized Cyclic Enones by 4π Electrocyclic Ring Opening Heck Matsuda Arylation Sequence -- Asymmetric Organocatalytic [2+2] Cycloaddition Affording Bicyclo[n.2.0]alkenes -- Conclusion -- Experiments.  aThis book explains the existence of the intermediate using two approaches: computational chemistry and coordination chemistry. In this book, the author has developed new methods for synthesizing medium-sized cycloalkenes by utilizing the 4π-electrocyclic reaction of fused-cyclobutenes. The fundamental and most important strategy and feature of the work are as follows: first, cyclobutene is used as a readily available raw material with high-strain energy to generate more strained medium-sized cis,trans-cycloalkadiene molecules. Second, by judiciously selecting the reaction conditions, the short-lived intermediate (medium-sized cis,trans-cycloalkadiene) can be converted to medium-sized cis- or trans-cycloalkenes. For the former, the generation of the medium-sized cis,trans-cycloalkadiene intermediate is greatly affected by the substituent on the cyclobutene, and there are few examples of its generation confirmed at room temperature. Regarding the latter, the synthesis of trans-cycloalkenes is noteworthy in terms of establishing a new synthetic methodology and providing one of the few asymmetric synthesis methods, which has not been achieved before. Readers of this book can gain novel insights into strained molecules involved not only in small-sized cycloalkenes but also in medium-sized ones. 0aChemistry, Organic.965325 0aChemistry. 0aMedicinal chemistry. 0aPharmacology.96784414aOrganic Chemistry.96532724aChemical Synthesis.96882224aMedicinal Chemistry.24aPharmacology.9678442 aSpringerLink (Online service)0 tSpringer Nature eBook08iPrinted edition:z978981970786708iPrinted edition:z978981970788108iPrinted edition:z9789819707898 0aSpringer Theses, Recognizing Outstanding Ph.D. Research,x2190-506196637040uhttps://doi.org/10.1007/978-981-97-0787-4  aZDB-2-CMS  aZDB-2-SXC  c58977d58977