Efficient trans-Selectivity in the Cyclocondensation of (S)-2-[2-(p-Tolylsulfinyl)phenyl]acetaldehyde with Activated Dienes Catalyzed by Yb(OTf)3
Reactions of (S)-2-[2-(p-tolylsulfinyl)phenyl]acetaldehyde 1 with Danishefsky's and related dienes took place in the presence of Yb(OTf)3 in a completely stereoselective manner, mediated by a remote sulfinyl group (1,5-asymmetric induction), to afford the corresponding 2,3-dihydro-4H-pyran-4-on...
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| Veröffentlicht in: | Journal of organic chemistry 2006-09, Vol.71 (20), p.7683-7689 |
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| container_issue | 20 |
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| container_title | Journal of organic chemistry |
| container_volume | 71 |
| creator | García Ruano, José L Fernández-Ibáñez, M. Ángeles Maestro, M. Carmen |
| description | Reactions of (S)-2-[2-(p-tolylsulfinyl)phenyl]acetaldehyde 1 with Danishefsky's and related dienes took place in the presence of Yb(OTf)3 in a completely stereoselective manner, mediated by a remote sulfinyl group (1,5-asymmetric induction), to afford the corresponding 2,3-dihydro-4H-pyran-4-ones. These reactions followed a stepwise mechanism, as was corroborated by isolation of the corresponding intermediates, with a high level of trans-selectivity for 4-methyl-substituted dienes. Treatment of the adducts with Raney Ni provided concomitant cleavage of the C−S bond and reduction of the conjugated carbonyl grouping. |
| doi_str_mv | 10.1021/jo061128n |
| format | Article |
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Treatment of the adducts with Raney Ni provided concomitant cleavage of the C−S bond and reduction of the conjugated carbonyl grouping.</description><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2006</creationdate><recordtype>article</recordtype><recordid>eNpt0MtuEzEUBmALgWgoLHgB5A0oWRh8GXtmllUoFKhopASJi5Dl8Rwrbp2ZMHaA4S14Y1wlajZ4cyT70--jH6GnjL5klLNX1z1VjPGqu4cmTHJKVE2L-2hCKedEcCVO0KMYr2k-UsqH6ISpupaqLCbo77lz3nroEk6D6SJZQgCb_E-fRuw7nNaA56MNve27Frpoku873Ds8Xc4IJ984mW7Jqg9jiLvgfDeG2XYNeXw3FpIJLazHFvAvn9b47DbXJGjx6_whRDw3WYx_8kUz4i_N9GrlZuIxeuBMiPDkME_Rpzfnq_kFubx6-25-dkkMr1UiTVU2hRWs5YWgYItCOmF4WbLKVgCikaqVtqyZo7ZtJANXC94wW1RGiUqUXJyiF_vc7dD_2EFMeuOjhRBMB_0ualVVlap5meFsD-3QxziA09vBb8wwakb1bf_6rv9snx1Cd80G2qM8FJ7B8wMw0ZrgcufWx6OrmCyKkmVH9s7HBL_v3s1wo1UpSqlXi6VefFYfFxdfP-j3x1xjY95nN3S5u_8s-A-zHqlb</recordid><startdate>20060929</startdate><enddate>20060929</enddate><creator>García Ruano, José L</creator><creator>Fernández-Ibáñez, M. 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Chem</addtitle><date>2006-09-29</date><risdate>2006</risdate><volume>71</volume><issue>20</issue><spage>7683</spage><epage>7689</epage><pages>7683-7689</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>Reactions of (S)-2-[2-(p-tolylsulfinyl)phenyl]acetaldehyde 1 with Danishefsky's and related dienes took place in the presence of Yb(OTf)3 in a completely stereoselective manner, mediated by a remote sulfinyl group (1,5-asymmetric induction), to afford the corresponding 2,3-dihydro-4H-pyran-4-ones. These reactions followed a stepwise mechanism, as was corroborated by isolation of the corresponding intermediates, with a high level of trans-selectivity for 4-methyl-substituted dienes. Treatment of the adducts with Raney Ni provided concomitant cleavage of the C−S bond and reduction of the conjugated carbonyl grouping.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>16995674</pmid><doi>10.1021/jo061128n</doi><tpages>7</tpages></addata></record> |
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| ispartof | Journal of organic chemistry, 2006-09, Vol.71 (20), p.7683-7689 |
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| language | eng |
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| source | American Chemical Society Journals |
| subjects | Chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives Organic chemistry Preparations and properties |
| title | Efficient trans-Selectivity in the Cyclocondensation of (S)-2-[2-(p-Tolylsulfinyl)phenyl]acetaldehyde with Activated Dienes Catalyzed by Yb(OTf)3 |
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