β-Cleavage of Bis(homoallylic) Potassium Alkoxides. Two-Step Preparation of Propenyl Ketones from Carboxylic Esters. Synthesis of ar-Turmerone, α-Damascone, β-Damascone, and β-Damascenone
The transformation of 36 bis(homoallylic) alcohols VII to alkenones IX and X via β‐cleavage of their potassium alkoxides VIIa in HMPA has been investigated (cf. Scheme 2). These studies have established an order of β‐cleavage for 2‐propenyl, 1‐methyl‐2propenyl, 2‐methyl‐2‐propenyl, 1,1‐dimethyl‐2pro...
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| Veröffentlicht in: | Helvetica chimica acta 1987-11, Vol.70 (7), p.1858-1878 |
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| creator | Snowden, Roger L. Linder, Simon M. Muller, Bernard L. Schulte-Elte, Karl H. |
| description | The transformation of 36 bis(homoallylic) alcohols VII to alkenones IX and X via β‐cleavage of their potassium alkoxides VIIa in HMPA has been investigated (cf. Scheme 2). These studies have established an order of β‐cleavage for 2‐propenyl, 1‐methyl‐2propenyl, 2‐methyl‐2‐propenyl, 1,1‐dimethyl‐2propenyl, and benzyl groups in alkoxides 49a–56a and have allowed a comparison between the β‐cleavege reaction and the oxy‐Cope rearrangement in alkoxides 74a–83a. As illustrative syntheti applications, a two‐step preparatio of propenyl ketones 15–42 from carboxylic esters is described, together with syntheses of ar‐turmerone (48), α‐damascone ((E)‐71), β‐damascone ((E)‐109), and β‐damascenone ((E)‐111). |
| doi_str_mv | 10.1002/hlca.19870700721 |
| format | Article |
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Two-Step Preparation of Propenyl Ketones from Carboxylic Esters. Synthesis of ar-Turmerone, α-Damascone, β-Damascone, and β-Damascenone</title><source>Wiley Online Library Journals Frontfile Complete</source><creator>Snowden, Roger L. ; Linder, Simon M. ; Muller, Bernard L. ; Schulte-Elte, Karl H.</creator><creatorcontrib>Snowden, Roger L. ; Linder, Simon M. ; Muller, Bernard L. ; Schulte-Elte, Karl H.</creatorcontrib><description>The transformation of 36 bis(homoallylic) alcohols VII to alkenones IX and X via β‐cleavage of their potassium alkoxides VIIa in HMPA has been investigated (cf. Scheme 2). These studies have established an order of β‐cleavage for 2‐propenyl, 1‐methyl‐2propenyl, 2‐methyl‐2‐propenyl, 1,1‐dimethyl‐2propenyl, and benzyl groups in alkoxides 49a–56a and have allowed a comparison between the β‐cleavege reaction and the oxy‐Cope rearrangement in alkoxides 74a–83a. As illustrative syntheti applications, a two‐step preparatio of propenyl ketones 15–42 from carboxylic esters is described, together with syntheses of ar‐turmerone (48), α‐damascone ((E)‐71), β‐damascone ((E)‐109), and β‐damascenone ((E)‐111).</description><identifier>ISSN: 0018-019X</identifier><identifier>EISSN: 1522-2675</identifier><identifier>DOI: 10.1002/hlca.19870700721</identifier><identifier>CODEN: HCACAV</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag GmbH</publisher><subject>Aliphatic compounds ; Chemistry ; Exact sciences and technology ; Organic chemistry ; Preparations and properties</subject><ispartof>Helvetica chimica acta, 1987-11, Vol.70 (7), p.1858-1878</ispartof><rights>Copyright © 1987 Verlag GmbH & Co. KGaA, Weinheim</rights><rights>1988 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c2791-9fd43cc6f466395cedaff9543a7112abddb12d5a68a7d5ecbfa3525b1889b5c53</citedby><cites>FETCH-LOGICAL-c2791-9fd43cc6f466395cedaff9543a7112abddb12d5a68a7d5ecbfa3525b1889b5c53</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fhlca.19870700721$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fhlca.19870700721$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,777,781,1412,27905,27906,45555,45556</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=7778359$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>Snowden, Roger L.</creatorcontrib><creatorcontrib>Linder, Simon M.</creatorcontrib><creatorcontrib>Muller, Bernard L.</creatorcontrib><creatorcontrib>Schulte-Elte, Karl H.</creatorcontrib><title>β-Cleavage of Bis(homoallylic) Potassium Alkoxides. 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As illustrative syntheti applications, a two‐step preparatio of propenyl ketones 15–42 from carboxylic esters is described, together with syntheses of ar‐turmerone (48), α‐damascone ((E)‐71), β‐damascone ((E)‐109), and β‐damascenone ((E)‐111).</description><subject>Aliphatic compounds</subject><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><issn>0018-019X</issn><issn>1522-2675</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1987</creationdate><recordtype>article</recordtype><recordid>eNqFkcFu1DAQhiMEEkvhztEHDiDhxXbWcXzgsA1lCyxlpS6CmzVxbDbUiSM7pZvHoi_AG_SZSLSolBOn0T-a75_R_EnylJI5JYS92jkNcypzQQQhgtF7yYxyxjDLBL-fzAihOSZUfn2YPIrxOyFESiJmya-ba1w4Az_gm0HeouM6Pt_5xoNzg6v1C7TxPcRYXzZo6S78vq5MnKPtlcfnvenQJpgOAvS1byd6E3xn2sGhD6b3rYnIBt-gAkLp95MdOom9CaPB-dD2OxPrOFEQ8PYyNCaMyEt08xO_gQaiPqjruwra6m_HtGPvcfLAgovmyZ96lHx-e7ItTvH60-pdsVxjzYSkWNpqkWqd2UWWpZJrU4G1ki9SEJQyKKuqpKzikOUgKm50aSHljJc0z2XJNU-PEnLw1cHHGIxVXagbCIOiRE0BqCkAdSeAEXl2QLrxWHA2QKvreMsJIfKUy3Hs9WHsqnZm-K-tOl0Xy3_X4ANfj7_d3_IQLlQmUsHVl7OVev9xsV6dbZiS6W9WT64m</recordid><startdate>19871104</startdate><enddate>19871104</enddate><creator>Snowden, Roger L.</creator><creator>Linder, Simon M.</creator><creator>Muller, Bernard L.</creator><creator>Schulte-Elte, Karl H.</creator><general>WILEY-VCH Verlag GmbH</general><general>WILEY‐VCH Verlag GmbH</general><general>Wiley</general><scope>BSCLL</scope><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>19871104</creationdate><title>β-Cleavage of Bis(homoallylic) Potassium Alkoxides. Two-Step Preparation of Propenyl Ketones from Carboxylic Esters. Synthesis of ar-Turmerone, α-Damascone, β-Damascone, and β-Damascenone</title><author>Snowden, Roger L. ; Linder, Simon M. ; Muller, Bernard L. ; Schulte-Elte, Karl H.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c2791-9fd43cc6f466395cedaff9543a7112abddb12d5a68a7d5ecbfa3525b1889b5c53</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1987</creationdate><topic>Aliphatic compounds</topic><topic>Chemistry</topic><topic>Exact sciences and technology</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Snowden, Roger L.</creatorcontrib><creatorcontrib>Linder, Simon M.</creatorcontrib><creatorcontrib>Muller, Bernard L.</creatorcontrib><creatorcontrib>Schulte-Elte, Karl H.</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>CrossRef</collection><jtitle>Helvetica chimica acta</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Snowden, Roger L.</au><au>Linder, Simon M.</au><au>Muller, Bernard L.</au><au>Schulte-Elte, Karl H.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>β-Cleavage of Bis(homoallylic) Potassium Alkoxides. Two-Step Preparation of Propenyl Ketones from Carboxylic Esters. Synthesis of ar-Turmerone, α-Damascone, β-Damascone, and β-Damascenone</atitle><jtitle>Helvetica chimica acta</jtitle><addtitle>HCA</addtitle><date>1987-11-04</date><risdate>1987</risdate><volume>70</volume><issue>7</issue><spage>1858</spage><epage>1878</epage><pages>1858-1878</pages><issn>0018-019X</issn><eissn>1522-2675</eissn><coden>HCACAV</coden><abstract>The transformation of 36 bis(homoallylic) alcohols VII to alkenones IX and X via β‐cleavage of their potassium alkoxides VIIa in HMPA has been investigated (cf. Scheme 2). These studies have established an order of β‐cleavage for 2‐propenyl, 1‐methyl‐2propenyl, 2‐methyl‐2‐propenyl, 1,1‐dimethyl‐2propenyl, and benzyl groups in alkoxides 49a–56a and have allowed a comparison between the β‐cleavege reaction and the oxy‐Cope rearrangement in alkoxides 74a–83a. As illustrative syntheti applications, a two‐step preparatio of propenyl ketones 15–42 from carboxylic esters is described, together with syntheses of ar‐turmerone (48), α‐damascone ((E)‐71), β‐damascone ((E)‐109), and β‐damascenone ((E)‐111).</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag GmbH</pub><doi>10.1002/hlca.19870700721</doi><tpages>21</tpages></addata></record> |
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| ispartof | Helvetica chimica acta, 1987-11, Vol.70 (7), p.1858-1878 |
| issn | 0018-019X 1522-2675 |
| language | eng |
| recordid | cdi_crossref_primary_10_1002_hlca_19870700721 |
| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Aliphatic compounds Chemistry Exact sciences and technology Organic chemistry Preparations and properties |
| title | β-Cleavage of Bis(homoallylic) Potassium Alkoxides. Two-Step Preparation of Propenyl Ketones from Carboxylic Esters. Synthesis of ar-Turmerone, α-Damascone, β-Damascone, and β-Damascenone |
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