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Microwave-Assisted Organocatalytic Quadruple Domino Reactions of Acetaldehyde and Nitroalkenes
Abstract A microwave-assisted, organocatalytic domino Michael/Henry condensation/Michael/aldol condensation reaction has been developed. Employing acetaldehyde and nitroalkenes as substrates, this quadruple cascade allows an efficient asymmetric synthesis of trisubstituted cyclohexene carbaldehydes...
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| Published in: | Synthesis (Stuttgart) 2010-02, Vol.2010 (4), p.567-572 |
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| Main Authors: | , , |
| Format: | Article |
| Language: | English |
| Citations: | Items that cite this one |
| Online Access: | Get full text |
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| cited_by | cdi_FETCH-LOGICAL-c343t-257ae74b0e78ba796fc1641852c589f24df8437fbfef74dfa80440650857fb5a3 |
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| container_end_page | 572 |
| container_issue | 4 |
| container_start_page | 567 |
| container_title | Synthesis (Stuttgart) |
| container_volume | 2010 |
| creator | Enders, Dieter Krüll, Ralf Bettray, Wolfgang |
| description | Abstract
A microwave-assisted, organocatalytic domino Michael/Henry
condensation/Michael/aldol condensation reaction
has been developed. Employing acetaldehyde and nitroalkenes as substrates, this
quadruple cascade allows an efficient asymmetric synthesis of trisubstituted
cyclohexene carbaldehydes in moderate to good yields (25-45%)
and high enantioselectivities (ee = 89
to >99%). ESI-MS measurements were carried out
to support the proposed complex catalytic cycle. |
| doi_str_mv | 10.1055/s-0029-1217146 |
| format | article |
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A microwave-assisted, organocatalytic domino Michael/Henry
condensation/Michael/aldol condensation reaction
has been developed. Employing acetaldehyde and nitroalkenes as substrates, this
quadruple cascade allows an efficient asymmetric synthesis of trisubstituted
cyclohexene carbaldehydes in moderate to good yields (25-45%)
and high enantioselectivities (ee = 89
to >99%). ESI-MS measurements were carried out
to support the proposed complex catalytic cycle.</description><identifier>ISSN: 0039-7881</identifier><identifier>EISSN: 1437-210X</identifier><identifier>DOI: 10.1055/s-0029-1217146</identifier><language>eng</language><ispartof>Synthesis (Stuttgart), 2010-02, Vol.2010 (4), p.567-572</ispartof><rights>Georg Thieme Verlag Stuttgart ˙ New York</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c343t-257ae74b0e78ba796fc1641852c589f24df8437fbfef74dfa80440650857fb5a3</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-0029-1217146.pdf$$EPDF$$P50$$Gthieme$$H</linktopdf><linktohtml>$$Uhttps://www.thieme-connect.de/products/ejournals/html/10.1055/s-0029-1217146$$EHTML$$P50$$Gthieme$$H</linktohtml><link.rule.ids>314,780,784,3017,3018,27924,27925,54559,54560</link.rule.ids></links><search><creatorcontrib>Enders, Dieter</creatorcontrib><creatorcontrib>Krüll, Ralf</creatorcontrib><creatorcontrib>Bettray, Wolfgang</creatorcontrib><title>Microwave-Assisted Organocatalytic Quadruple Domino Reactions of Acetaldehyde and Nitroalkenes</title><title>Synthesis (Stuttgart)</title><addtitle>Synthesis</addtitle><description>Abstract
A microwave-assisted, organocatalytic domino Michael/Henry
condensation/Michael/aldol condensation reaction
has been developed. Employing acetaldehyde and nitroalkenes as substrates, this
quadruple cascade allows an efficient asymmetric synthesis of trisubstituted
cyclohexene carbaldehydes in moderate to good yields (25-45%)
and high enantioselectivities (ee = 89
to >99%). ESI-MS measurements were carried out
to support the proposed complex catalytic cycle.</description><issn>0039-7881</issn><issn>1437-210X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2010</creationdate><recordtype>article</recordtype><recordid>eNp1kM1OwzAQhC0EEqVw5ewXcFknduwcq_JTpEIFAokTkeusqUsaV3YK6tuTqr1yWs1qZrXzEXLNYcRBypvEALKS8YwrLooTMuAiVyzj8HFKBgB5yZTW_JxcpLQCAJXl5YB8Pnkbw6_5QTZOyacOazqPX6YN1nSm2XXe0petqeN20yC9DWvfBvqKxnY-tIkGR8cWe2ONy12N1LQ1ffZdDKb5xhbTJTlzpkl4dZxD8n5_9zaZstn84XEynjGbi7xjmVQGlVgAKr0wqiyc5YXgWmZW6tJlona6L-MWDp3qhdEgBBQStOyX0uRDMjrc7cukFNFVm-jXJu4qDtWeTpWqPZ3qSKcPsEOgW3pcY7UK29j2H_7n_wMcUWdZ</recordid><startdate>20100201</startdate><enddate>20100201</enddate><creator>Enders, Dieter</creator><creator>Krüll, Ralf</creator><creator>Bettray, Wolfgang</creator><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20100201</creationdate><title>Microwave-Assisted Organocatalytic Quadruple Domino Reactions of Acetaldehyde and Nitroalkenes</title><author>Enders, Dieter ; Krüll, Ralf ; Bettray, Wolfgang</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c343t-257ae74b0e78ba796fc1641852c589f24df8437fbfef74dfa80440650857fb5a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2010</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Enders, Dieter</creatorcontrib><creatorcontrib>Krüll, Ralf</creatorcontrib><creatorcontrib>Bettray, Wolfgang</creatorcontrib><collection>CrossRef</collection><jtitle>Synthesis (Stuttgart)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Enders, Dieter</au><au>Krüll, Ralf</au><au>Bettray, Wolfgang</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Microwave-Assisted Organocatalytic Quadruple Domino Reactions of Acetaldehyde and Nitroalkenes</atitle><jtitle>Synthesis (Stuttgart)</jtitle><addtitle>Synthesis</addtitle><date>2010-02-01</date><risdate>2010</risdate><volume>2010</volume><issue>4</issue><spage>567</spage><epage>572</epage><pages>567-572</pages><issn>0039-7881</issn><eissn>1437-210X</eissn><abstract>Abstract
A microwave-assisted, organocatalytic domino Michael/Henry
condensation/Michael/aldol condensation reaction
has been developed. Employing acetaldehyde and nitroalkenes as substrates, this
quadruple cascade allows an efficient asymmetric synthesis of trisubstituted
cyclohexene carbaldehydes in moderate to good yields (25-45%)
and high enantioselectivities (ee = 89
to >99%). ESI-MS measurements were carried out
to support the proposed complex catalytic cycle.</abstract><doi>10.1055/s-0029-1217146</doi><tpages>6</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0039-7881 |
| ispartof | Synthesis (Stuttgart), 2010-02, Vol.2010 (4), p.567-572 |
| issn | 0039-7881 1437-210X |
| language | eng |
| recordid | cdi_crossref_primary_10_1055_s_0029_1217146 |
| source | Thieme Connect |
| title | Microwave-Assisted Organocatalytic Quadruple Domino Reactions of Acetaldehyde and Nitroalkenes |
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