2017
DOI: 10.1055/s-0036-1588703
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[3+2] Annulation of Donor–Acceptor Cyclopropanes with Vinyl Azides

Abstract: A Sc(OTf) 3 -catalyzed reaction of vinyl azides with donor-acceptor cyclopropanes affords highly functionalized azidocyclopentanes in a diastereoselective fashion. The resulting azidocyclopentanes could be transformed into various cyclic scaffolds.

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Cited by 19 publications
(5 citation statements)
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“…Subsequently, the scope of this ring expansion reaction of 2-azidoBCHs was tested (Scheme ). In all cases, migration of secondary carbon occurred exclusively, leading to corresponding 3-aza-BCHepes in a highly chemoselective manner, probably due to the steric hindrance of the quaternary carbon at bridgehead position. , The expected structure of 5a was confirmed by X-ray diffraction analysis of its single crystal . Functional groups such as Me, OMe, Cl, and COOMe on the phenyl rings of BCBs had no influence on the rearrangement, and the related 3-aza-BCHepes ( 5b–5i ) were obtained in good yields (78–88%).…”
Section: Resultsmentioning
confidence: 71%
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“…Subsequently, the scope of this ring expansion reaction of 2-azidoBCHs was tested (Scheme ). In all cases, migration of secondary carbon occurred exclusively, leading to corresponding 3-aza-BCHepes in a highly chemoselective manner, probably due to the steric hindrance of the quaternary carbon at bridgehead position. , The expected structure of 5a was confirmed by X-ray diffraction analysis of its single crystal . Functional groups such as Me, OMe, Cl, and COOMe on the phenyl rings of BCBs had no influence on the rearrangement, and the related 3-aza-BCHepes ( 5b–5i ) were obtained in good yields (78–88%).…”
Section: Resultsmentioning
confidence: 71%
“…Next, we focused on the study of constructing 3-aza-BCHepes. Although Lewis acid-catalyzed reactions of vinyl azides and donor–acceptor cyclopropanes have been reported on the preparation of tetrahydropyridines, , synthesizing conformationally rigid 3-aza-BCHepes poses challenges with regard to the reactivity of (3 + 2) annulation of BCBs and chemoselectivity of ring expansion of bicyclic skeletons. Notably, to the best of our knowledge, Lewis acid-catalyzed (3 + 2) annulation of BCBs with electron-rich alkenes is still unknown. To this end, (3 + 2) annulation of 1a and 2a was first investigated.…”
Section: Resultsmentioning
confidence: 99%
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“…2017 年, López 等 [19] 报道了 Cu(I)催化的烯基叠氮与 图式 7 重氮酯与乙烯基叠氮的环丙烷化反应 Scheme 7 Cyclopropanation of diazo esters and azido alkenes 给体-受体环丙烷由于张力作用极易开环形成 1,3-两性离子, 因此在有机合成中常被用到[3+n]环加成反 应中 [20] . 2017 年, Banerjee 课题组 [21] 同年, Chiba 课题组 [22] 也报道了 Sc(OTf) (Scheme 11, c) [25] .…”
Section: 环丙烷化和[3+2]环加成反应unclassified
“…Therefore, they commonly react as three‐atom framework, and the 1,3‐dipole intermediates are able to undergo various transformations such as ring‐opening reactions with electrophilic and nucleophilic components, and cycloaddition reactions . Recently, the [3+2] cycloaddition of D−A cyclopropanes with various double bonds such as nitrones, aldehydes, benzothiazoles, and olefins have been investigated. In 2005, a catalytic synthesis of 2,5‐disubstituted tetrahydrofurans from D−A cyclopropanes and aldehydes through [3+2] cycloaddition had been developed by Johnson and co‐workers .…”
Section: Introductionmentioning
confidence: 99%