Stereoselectivity in Trimethylenemethane (TMM) Diyl Mediated Cycloaddition Reaction to Angularly Fused Triquinanes
A thorough study on the diastereoselectivity in the TMM diyl mediated [2+3] cycloaddition reaction of monosubstituted linear substrates to form angularly fused triquinanes was carried out. Substitution at position 3 provided complete diastereoselectivity, while positions 1 and 4 induced marginal ste...
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| Veröffentlicht in: | Chemistry, an Asian journal an Asian journal, 2011-02, Vol.6 (2), p.646-651 |
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| creator | Yoon, Yeokwon Kang, Taek Lee, Hee-Yoon |
| description | A thorough study on the diastereoselectivity in the TMM diyl mediated [2+3] cycloaddition reaction of monosubstituted linear substrates to form angularly fused triquinanes was carried out. Substitution at position 3 provided complete diastereoselectivity, while positions 1 and 4 induced marginal stereoselectivity. Position 2 did not show any influence on the diastereoselectivity. Position 4 turned out to be incompatible with the cycloaddition reaction as the carbene intermediate underwent OSi bond insertion to form a dihydrofuran ring.
Stereoinduction: A thorough study on the diastereoselectivity in the TMM diyl mediated [2+3] cycloaddtion reaction of monosubstituted linear substrates to form angularly fused triquinanes was carried out. Substitution at position 3 provided complete diastereoselectivity, whilst positions 1 and 4 induced marginal stereoselectivity. Position 2 did not show any influence on the diastereoselectivity. Position 4 was incompatible with the cycloaddition reaction, as the carbene intermediate underwent OSi bond insertion to form a dihydrofuran ring. |
| doi_str_mv | 10.1002/asia.201000672 |
| format | Article |
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Stereoinduction: A thorough study on the diastereoselectivity in the TMM diyl mediated [2+3] cycloaddtion reaction of monosubstituted linear substrates to form angularly fused triquinanes was carried out. Substitution at position 3 provided complete diastereoselectivity, whilst positions 1 and 4 induced marginal stereoselectivity. Position 2 did not show any influence on the diastereoselectivity. Position 4 was incompatible with the cycloaddition reaction, as the carbene intermediate underwent OSi bond insertion to form a dihydrofuran ring.</description><identifier>ISSN: 1861-4728</identifier><identifier>EISSN: 1861-471X</identifier><identifier>DOI: 10.1002/asia.201000672</identifier><identifier>PMID: 21254438</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>carbenes ; Chemistry ; cycloaddition ; stereoselectivity ; trimethylenemethane ; triquinane</subject><ispartof>Chemistry, an Asian journal, 2011-02, Vol.6 (2), p.646-651</ispartof><rights>Copyright © 2011 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><rights>Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4102-6b62f7b8a2ea1774ef7842fbb91d1cee436866b1b76f67383c8dc6a0b0a2b8fc3</citedby><cites>FETCH-LOGICAL-c4102-6b62f7b8a2ea1774ef7842fbb91d1cee436866b1b76f67383c8dc6a0b0a2b8fc3</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%2Fasia.201000672$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fasia.201000672$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/21254438$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Yoon, Yeokwon</creatorcontrib><creatorcontrib>Kang, Taek</creatorcontrib><creatorcontrib>Lee, Hee-Yoon</creatorcontrib><title>Stereoselectivity in Trimethylenemethane (TMM) Diyl Mediated Cycloaddition Reaction to Angularly Fused Triquinanes</title><title>Chemistry, an Asian journal</title><addtitle>Chem. Asian J</addtitle><description>A thorough study on the diastereoselectivity in the TMM diyl mediated [2+3] cycloaddition reaction of monosubstituted linear substrates to form angularly fused triquinanes was carried out. Substitution at position 3 provided complete diastereoselectivity, while positions 1 and 4 induced marginal stereoselectivity. Position 2 did not show any influence on the diastereoselectivity. Position 4 turned out to be incompatible with the cycloaddition reaction as the carbene intermediate underwent OSi bond insertion to form a dihydrofuran ring.
Stereoinduction: A thorough study on the diastereoselectivity in the TMM diyl mediated [2+3] cycloaddtion reaction of monosubstituted linear substrates to form angularly fused triquinanes was carried out. Substitution at position 3 provided complete diastereoselectivity, whilst positions 1 and 4 induced marginal stereoselectivity. Position 2 did not show any influence on the diastereoselectivity. Position 4 was incompatible with the cycloaddition reaction, as the carbene intermediate underwent OSi bond insertion to form a dihydrofuran ring.</description><subject>carbenes</subject><subject>Chemistry</subject><subject>cycloaddition</subject><subject>stereoselectivity</subject><subject>trimethylenemethane</subject><subject>triquinane</subject><issn>1861-4728</issn><issn>1861-471X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><recordid>eNqFkUFv1DAUhCMEoqVw5YgscaA9ZLEdx3aOq6XtVuqCoIvKzbKdF3DxJq3tAPn39bJlhbhwenP4ZvQ0UxQvCZ4RjOlbHZ2eUZw15oI-Kg6J5KRkgnx5vNdUHhTPYrzBuKa4kU-LA0pozVglD4twlSDAEMGDTe6HSxNyPVoHt4H0bfLQw1boHtDxerU6Qe_c5NEKWqcTtGgxWT_otnXJDT36BNr-FmlA8_7r6HXwEzobYyZz4t3o-hwUnxdPOu0jvHi4R8Xns9P1Yllefji_WMwvS8sIpiU3nHbCSE1BEyEYdEIy2hnTkJZYAFZxybkhRvCOi0pWVraWa2ywpkZ2tjoq3uxyb8NwN0JMauOiBe_zE8MYlWS8ycU1dSZf_0PeDGPo83OK1EQwmrvlmZrtKBuGGAN06jbXpMOkCFbbMdR2DLUfIxtePcSOZgPtHv_TfgaaHfDTeZj-E6fmVxfzv8PLndfFBL_2Xh2-q9yGqNX1-3NVE7pcL68_qrq6B9tfplw</recordid><startdate>20110201</startdate><enddate>20110201</enddate><creator>Yoon, Yeokwon</creator><creator>Kang, Taek</creator><creator>Lee, Hee-Yoon</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>K9.</scope><scope>7X8</scope></search><sort><creationdate>20110201</creationdate><title>Stereoselectivity in Trimethylenemethane (TMM) Diyl Mediated Cycloaddition Reaction to Angularly Fused Triquinanes</title><author>Yoon, Yeokwon ; Kang, Taek ; Lee, Hee-Yoon</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4102-6b62f7b8a2ea1774ef7842fbb91d1cee436866b1b76f67383c8dc6a0b0a2b8fc3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>carbenes</topic><topic>Chemistry</topic><topic>cycloaddition</topic><topic>stereoselectivity</topic><topic>trimethylenemethane</topic><topic>triquinane</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Yoon, Yeokwon</creatorcontrib><creatorcontrib>Kang, Taek</creatorcontrib><creatorcontrib>Lee, Hee-Yoon</creatorcontrib><collection>Istex</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Chemistry, an Asian journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Yoon, Yeokwon</au><au>Kang, Taek</au><au>Lee, Hee-Yoon</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Stereoselectivity in Trimethylenemethane (TMM) Diyl Mediated Cycloaddition Reaction to Angularly Fused Triquinanes</atitle><jtitle>Chemistry, an Asian journal</jtitle><addtitle>Chem. Asian J</addtitle><date>2011-02-01</date><risdate>2011</risdate><volume>6</volume><issue>2</issue><spage>646</spage><epage>651</epage><pages>646-651</pages><issn>1861-4728</issn><eissn>1861-471X</eissn><abstract>A thorough study on the diastereoselectivity in the TMM diyl mediated [2+3] cycloaddition reaction of monosubstituted linear substrates to form angularly fused triquinanes was carried out. Substitution at position 3 provided complete diastereoselectivity, while positions 1 and 4 induced marginal stereoselectivity. Position 2 did not show any influence on the diastereoselectivity. Position 4 turned out to be incompatible with the cycloaddition reaction as the carbene intermediate underwent OSi bond insertion to form a dihydrofuran ring.
Stereoinduction: A thorough study on the diastereoselectivity in the TMM diyl mediated [2+3] cycloaddtion reaction of monosubstituted linear substrates to form angularly fused triquinanes was carried out. Substitution at position 3 provided complete diastereoselectivity, whilst positions 1 and 4 induced marginal stereoselectivity. Position 2 did not show any influence on the diastereoselectivity. Position 4 was incompatible with the cycloaddition reaction, as the carbene intermediate underwent OSi bond insertion to form a dihydrofuran ring.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><pmid>21254438</pmid><doi>10.1002/asia.201000672</doi><tpages>6</tpages></addata></record> |
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| language | eng |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | carbenes Chemistry cycloaddition stereoselectivity trimethylenemethane triquinane |
| title | Stereoselectivity in Trimethylenemethane (TMM) Diyl Mediated Cycloaddition Reaction to Angularly Fused Triquinanes |
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