2015
DOI: 10.1021/acs.orglett.5b02516
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Synthesis of 6- and 7-Membered N-Heterocycles Using α-Phenylvinylsulfonium Salts

Abstract: General rightsThis document is made available in accordance with publisher policies. Please cite only the published version using the reference above. Full terms of use are available: http://www.bristol.ac.uk/pure/about/ebr-terms Supporting Information PlaceholderAbstract: A concise synthesis of stereodefined C-substituted morpholines, piperazines, azepines and oxazepines in moderate to excellent yields (27% to 75%) is reported by reaction of 1,2-or 1,3-amino alcohol/1,2-or 1,3-diamine with an α-phenylvinylsu… Show more

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Cited by 77 publications
(28 citation statements)
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“…Prompted by these findings, to further demonstrate the versatility and the synthetic utility of functionalised alkyl vinyl selenides bearing two ester groups, we sought to employ this class of organoselenium compounds for the construction of unsaturated seleniumcontaining δ-lactones. In addition to their occurrence in various pharmacologically relevant molecules, [33] chalcogen-containing six-membered heterocycles are useful in organic synthesis [34] and in medicinal chemistry. [14,35] Whilst sulfurated derivatives have been widely investigated for their properties, to the best of our knowledge, selenium-containing analogues have received less attention.…”
Section: Full Paper Ascwiley-vchdementioning
confidence: 99%
“…Prompted by these findings, to further demonstrate the versatility and the synthetic utility of functionalised alkyl vinyl selenides bearing two ester groups, we sought to employ this class of organoselenium compounds for the construction of unsaturated seleniumcontaining δ-lactones. In addition to their occurrence in various pharmacologically relevant molecules, [33] chalcogen-containing six-membered heterocycles are useful in organic synthesis [34] and in medicinal chemistry. [14,35] Whilst sulfurated derivatives have been widely investigated for their properties, to the best of our knowledge, selenium-containing analogues have received less attention.…”
Section: Full Paper Ascwiley-vchdementioning
confidence: 99%
“…A novel method for the synthesis of morpholines was reported by the Aggarwal group, which utilizes their α ‐arylvinyl sulfonium salt chemistry (Scheme ) . This transformation proceeds by an initial conjugate addition through the amino alcohol oxygen affording complete regioselectivity, followed by the S N 2 displacement of the sulfonium salt by the amine during cyclization which is the diastereoselectivity‐defining step of the reaction.…”
Section: Synthesis Of Morpholinesmentioning
confidence: 99%
“… Morpholine ring formation via α‐ arylvinyl sulfonium salt. Reagents and conditions: a) Cs 2 CO 3 (2×2 equiv), CH 2 Cl 2 , rt, 1–24 h; b) Na/naphthalene (3 equiv), DME (0.1 M), −78 °C, 30 min; c) HCl (1 M in diethyl ether, 1.5 equiv), rt, 5 min (yield: 55–75 %) . (DME: 1,2‐dimethoxyethane).…”
Section: Synthesis Of Morpholinesmentioning
confidence: 99%
“…In 2016 the Maulide group disclosed the results of their investigations into vinylsubstituted sulfonium ylides. Although Aggarwal had previously built on the ability of vinylsulfonium salts to undergo nucleophilic additions generating versatile sulfonium ylides in situ [31][32][33][34], no investigations into vinyl-substituted sulfonium ylides had been reported. When treated with an appropriate π-acidic catalyst, these compounds were shown to efficiently undergo S-to-O vinyl transfers (Scheme 15) [35].…”
Section: Transition Metals As π-Acid Catalystsmentioning
confidence: 99%