Cationic Cyclopentannelation of Allene Ethers
The variant of the Nazarov cyclization that makes use of allenyl ethers is suitable for the preparation of diverse, highly functionalized cyclopentenones. Three variants of the basic reaction, differing in the nature of the electrophile that is combined with the allene to prepare the precursor for t...
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| Veröffentlicht in: | Accounts of chemical research 2003-04, Vol.36 (4), p.284-290 |
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| container_title | Accounts of chemical research |
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| creator | Tius, Marcus A |
| description | The variant of the Nazarov cyclization that makes use of allenyl ethers is suitable for the preparation of diverse, highly functionalized cyclopentenones. Three variants of the basic reaction, differing in the nature of the electrophile that is combined with the allene to prepare the precursor for the pentadienyl cation, are described. One variant, which utilizes an α,β-unsaturated morpholino amide, has been successfully employed in an enantioselective version of the cyclopentannelation. |
| doi_str_mv | 10.1021/ar0200394 |
| format | Article |
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Three variants of the basic reaction, differing in the nature of the electrophile that is combined with the allene to prepare the precursor for the pentadienyl cation, are described. One variant, which utilizes an α,β-unsaturated morpholino amide, has been successfully employed in an enantioselective version of the cyclopentannelation.</description><identifier>ISSN: 0001-4842</identifier><identifier>EISSN: 1520-4898</identifier><identifier>DOI: 10.1021/ar0200394</identifier><identifier>PMID: 12693926</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Allyl Compounds - chemistry ; Amides - chemistry ; Cations ; Cyclization ; Cyclopentanes - chemical synthesis ; Ethers - chemistry ; Stereoisomerism</subject><ispartof>Accounts of chemical research, 2003-04, Vol.36 (4), p.284-290</ispartof><rights>Copyright © 2003 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a440t-7534d2e663d2be1ea258f3e370505526a3b633d086bfb642d09971229e3a51833</citedby><cites>FETCH-LOGICAL-a440t-7534d2e663d2be1ea258f3e370505526a3b633d086bfb642d09971229e3a51833</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/ar0200394$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ar0200394$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/12693926$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Tius, Marcus A</creatorcontrib><title>Cationic Cyclopentannelation of Allene Ethers</title><title>Accounts of chemical research</title><addtitle>Acc. 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| ispartof | Accounts of chemical research, 2003-04, Vol.36 (4), p.284-290 |
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| language | eng |
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| source | MEDLINE; American Chemical Society Journals |
| subjects | Allyl Compounds - chemistry Amides - chemistry Cations Cyclization Cyclopentanes - chemical synthesis Ethers - chemistry Stereoisomerism |
| title | Cationic Cyclopentannelation of Allene Ethers |
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