Iridium-catalyzed asymmetric [3+2] annulation of aromatic ketimines with alkynes CH activation: unexpected inversion of the enantioselectivity induced by protic acids
A cationic iridium/binap catalyst enabled the asymmetric [3+2] annulation of cyclic N -acyl ketimines with internal alkynes via CH activation to give spiroaminoindene derivatives with high enantioselectivity. The stereochemical course of this annulation was switchable by acid additives. The enantiod...
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| Veröffentlicht in: | Chemical communications (Cambridge, England) England), 2016-04, Vol.52 (34), p.5876-5879 |
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| container_title | Chemical communications (Cambridge, England) |
| container_volume | 52 |
| creator | Nagamoto, Midori Yamauchi, Daisuke Nishimura, Takahiro |
| description | A cationic iridium/binap catalyst enabled the asymmetric [3+2] annulation of cyclic
N
-acyl ketimines with internal alkynes
via
CH activation to give spiroaminoindene derivatives with high enantioselectivity. The stereochemical course of this annulation was switchable by acid additives.
The enantiodivergent synthesis of annulation products was achieved in the Ir-catalyzed asymmetric [3+2] annulation of cyclic
N
-acyl ketimines with internal alkynes
via
CH activation. |
| doi_str_mv | 10.1039/c6cc01398h |
| format | Article |
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N
-acyl ketimines with internal alkynes
via
CH activation to give spiroaminoindene derivatives with high enantioselectivity. The stereochemical course of this annulation was switchable by acid additives.
The enantiodivergent synthesis of annulation products was achieved in the Ir-catalyzed asymmetric [3+2] annulation of cyclic
N
-acyl ketimines with internal alkynes
via
CH activation.</description><identifier>ISSN: 1359-7345</identifier><identifier>EISSN: 1364-548X</identifier><identifier>DOI: 10.1039/c6cc01398h</identifier><ispartof>Chemical communications (Cambridge, England), 2016-04, Vol.52 (34), p.5876-5879</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27922,27923</link.rule.ids></links><search><creatorcontrib>Nagamoto, Midori</creatorcontrib><creatorcontrib>Yamauchi, Daisuke</creatorcontrib><creatorcontrib>Nishimura, Takahiro</creatorcontrib><title>Iridium-catalyzed asymmetric [3+2] annulation of aromatic ketimines with alkynes CH activation: unexpected inversion of the enantioselectivity induced by protic acids</title><title>Chemical communications (Cambridge, England)</title><description>A cationic iridium/binap catalyst enabled the asymmetric [3+2] annulation of cyclic
N
-acyl ketimines with internal alkynes
via
CH activation to give spiroaminoindene derivatives with high enantioselectivity. The stereochemical course of this annulation was switchable by acid additives.
The enantiodivergent synthesis of annulation products was achieved in the Ir-catalyzed asymmetric [3+2] annulation of cyclic
N
-acyl ketimines with internal alkynes
via
CH activation.</description><issn>1359-7345</issn><issn>1364-548X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><sourceid/><recordid>eNqFj09LxDAQxYMouP65eBfmLtXGtGvrdVHWuwdBZBnTWTpuk5YkXY0fyM-5qSx4dC4zj_m9N4wQFzK_lrmqb_Rc61yqumoPxEyqeZGVRfVyOM1lnd2pojwWJ95_5KlkWc3Ez5PjhkeTaQzYxW9qAH00hoJjDa_q6vYN0Nqxw8C9hX4N6HqThIYNBTZsycMnhxaw28RJLJaAOvD213APo6WvgXRIwWy35Pw-JrQEZNEmylNHk4NDTEwz6sS-RxhcP51BzY0_E0dr7Dyd7_upuHx8eF4sM-f1anBs0MXV3_Pqv_0OEodiDw</recordid><startdate>20160419</startdate><enddate>20160419</enddate><creator>Nagamoto, Midori</creator><creator>Yamauchi, Daisuke</creator><creator>Nishimura, Takahiro</creator><scope/></search><sort><creationdate>20160419</creationdate><title>Iridium-catalyzed asymmetric [3+2] annulation of aromatic ketimines with alkynes CH activation: unexpected inversion of the enantioselectivity induced by protic acids</title><author>Nagamoto, Midori ; Yamauchi, Daisuke ; Nishimura, Takahiro</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-rsc_primary_c6cc01398h3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><creationdate>2016</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Nagamoto, Midori</creatorcontrib><creatorcontrib>Yamauchi, Daisuke</creatorcontrib><creatorcontrib>Nishimura, Takahiro</creatorcontrib><jtitle>Chemical communications (Cambridge, England)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Nagamoto, Midori</au><au>Yamauchi, Daisuke</au><au>Nishimura, Takahiro</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Iridium-catalyzed asymmetric [3+2] annulation of aromatic ketimines with alkynes CH activation: unexpected inversion of the enantioselectivity induced by protic acids</atitle><jtitle>Chemical communications (Cambridge, England)</jtitle><date>2016-04-19</date><risdate>2016</risdate><volume>52</volume><issue>34</issue><spage>5876</spage><epage>5879</epage><pages>5876-5879</pages><issn>1359-7345</issn><eissn>1364-548X</eissn><abstract>A cationic iridium/binap catalyst enabled the asymmetric [3+2] annulation of cyclic
N
-acyl ketimines with internal alkynes
via
CH activation to give spiroaminoindene derivatives with high enantioselectivity. The stereochemical course of this annulation was switchable by acid additives.
The enantiodivergent synthesis of annulation products was achieved in the Ir-catalyzed asymmetric [3+2] annulation of cyclic
N
-acyl ketimines with internal alkynes
via
CH activation.</abstract><doi>10.1039/c6cc01398h</doi><tpages>4</tpages></addata></record> |
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| identifier | ISSN: 1359-7345 |
| ispartof | Chemical communications (Cambridge, England), 2016-04, Vol.52 (34), p.5876-5879 |
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| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| title | Iridium-catalyzed asymmetric [3+2] annulation of aromatic ketimines with alkynes CH activation: unexpected inversion of the enantioselectivity induced by protic acids |
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