Cooperative Catalysis for the Highly Diastereo‐ and Enantioselective [4+3]‐Cycloannulation of ortho‐Quinone Methides and Carbonyl Ylides
We describe herein a highly diastereo‐ and enantioselective [4+3]‐cycloannulation of ortho‐quinone methides and carbonyl ylides to furnish functionalized oxa‐bridged dibenzooxacines with excellent yields and stereoselectivity in a single synthetic step. The combination of rhodium and chiral phosphor...
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| Veröffentlicht in: | Angewandte Chemie International Edition 2020-03, Vol.59 (14), p.5536-5540 |
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| creator | Suneja, Arun Loui, Henning Jakob Schneider, Christoph |
| description | We describe herein a highly diastereo‐ and enantioselective [4+3]‐cycloannulation of ortho‐quinone methides and carbonyl ylides to furnish functionalized oxa‐bridged dibenzooxacines with excellent yields and stereoselectivity in a single synthetic step. The combination of rhodium and chiral phosphoric acid catalysis working in concert to generate both transient intermediates in situ provides direct access to complex bicyclic products with two quaternary and one tertiary stereogenic centers. The products may be further functionalized into valuable and enantiomerically highly enriched building blocks.
It takes two: A combination of Rh2(OAc)4 and a chiral phosphoric acid catalyzes the in situ generation of transient carbonyl ylides and chiral hydrogen‐bonded ortho‐quinone methides through cooperative catalytic cycles. These transient species then undergo a highly diastereo‐ and enantioselective cycloannulation to afford a broad range of functionalized oxa‐bridged dibenzooxacines featuring two quaternary and one tertiary stereogenic centers. |
| doi_str_mv | 10.1002/anie.201913603 |
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It takes two: A combination of Rh2(OAc)4 and a chiral phosphoric acid catalyzes the in situ generation of transient carbonyl ylides and chiral hydrogen‐bonded ortho‐quinone methides through cooperative catalytic cycles. These transient species then undergo a highly diastereo‐ and enantioselective cycloannulation to afford a broad range of functionalized oxa‐bridged dibenzooxacines featuring two quaternary and one tertiary stereogenic centers.</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.201913603</identifier><identifier>PMID: 31895488</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>asymmetric synthesis ; Carbonyl compounds ; carbonyl ylides ; Carbonyls ; Catalysis ; Communication ; Communications ; cooperative catalysis ; cycloannulation ; Enantiomers ; Intermediates ; ortho-quinone methides ; Phosphoric acid ; Quinones ; Rhodium ; Stereoselectivity</subject><ispartof>Angewandte Chemie International Edition, 2020-03, Vol.59 (14), p.5536-5540</ispartof><rights>2020 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.</rights><rights>2020. This article is published under http://creativecommons.org/licenses/by/4.0/ (the “License”). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c5713-9927a88458ae51dca2af892ce954171d3308155cc949ce672fe3f02008d0e01c3</citedby><cites>FETCH-LOGICAL-c5713-9927a88458ae51dca2af892ce954171d3308155cc949ce672fe3f02008d0e01c3</cites><orcidid>0000-0001-7392-9556</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fanie.201913603$$EPDF$$P50$$Gwiley$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.201913603$$EHTML$$P50$$Gwiley$$Hfree_for_read</linktohtml><link.rule.ids>230,314,780,784,885,1417,27924,27925,45574,45575</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/31895488$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Suneja, Arun</creatorcontrib><creatorcontrib>Loui, Henning Jakob</creatorcontrib><creatorcontrib>Schneider, Christoph</creatorcontrib><title>Cooperative Catalysis for the Highly Diastereo‐ and Enantioselective [4+3]‐Cycloannulation of ortho‐Quinone Methides and Carbonyl Ylides</title><title>Angewandte Chemie International Edition</title><addtitle>Angew Chem Int Ed Engl</addtitle><description>We describe herein a highly diastereo‐ and enantioselective [4+3]‐cycloannulation of ortho‐quinone methides and carbonyl ylides to furnish functionalized oxa‐bridged dibenzooxacines with excellent yields and stereoselectivity in a single synthetic step. The combination of rhodium and chiral phosphoric acid catalysis working in concert to generate both transient intermediates in situ provides direct access to complex bicyclic products with two quaternary and one tertiary stereogenic centers. The products may be further functionalized into valuable and enantiomerically highly enriched building blocks.
It takes two: A combination of Rh2(OAc)4 and a chiral phosphoric acid catalyzes the in situ generation of transient carbonyl ylides and chiral hydrogen‐bonded ortho‐quinone methides through cooperative catalytic cycles. These transient species then undergo a highly diastereo‐ and enantioselective cycloannulation to afford a broad range of functionalized oxa‐bridged dibenzooxacines featuring two quaternary and one tertiary stereogenic centers.</description><subject>asymmetric synthesis</subject><subject>Carbonyl compounds</subject><subject>carbonyl ylides</subject><subject>Carbonyls</subject><subject>Catalysis</subject><subject>Communication</subject><subject>Communications</subject><subject>cooperative catalysis</subject><subject>cycloannulation</subject><subject>Enantiomers</subject><subject>Intermediates</subject><subject>ortho-quinone methides</subject><subject>Phosphoric acid</subject><subject>Quinones</subject><subject>Rhodium</subject><subject>Stereoselectivity</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><sourceid>24P</sourceid><sourceid>WIN</sourceid><recordid>eNqFkcuKFDEUhoMozkW3LiXgRhiqzaWqk9oIQ9lzgVERdCEiIZM6NZUhnfQkVTPUzieQeUafxPT02F42rhJyvvORnx-hZ5TMKCHslfYWZozQmvI54Q_QLq0YLbgQ_GG-l5wXQlZ0B-2ldJl5Kcn8MdrhVNZVKeUu-t6EsIKoB3sNuNGDdlOyCXch4qEHfGIvejfhN1anASKEH99usfYtXnjtBxsSODB3q1_KA_41T5vJuKC9H11WBo9Dh0Mc-vXih9H64AG_haG3LaQ7UaPjefCTw5_d-u0JetRpl-Dp_bmPPh0tPjYnxdn749Pm8KwwlaC8qGsmtJRlJTVUtDWa6U7WzEBORQVtOSeSVpUxdVkbmAvWAe8II0S2BAg1fB-93nhX4_kSWgN-iNqpVbRLHScVtFV_T7zt1UW4ViJrKeFZ8PJeEMPVCGlQS5sMOKc9hDEpxjkjksiKZfTFP-hlGKPP8TIlapHLK-eZmm0oE0NKEbrtZyhR66rVumq1rTovPP8zwhb_1W0G6g1wYx1M_9Gpw3eni9_yn96luqY</recordid><startdate>20200327</startdate><enddate>20200327</enddate><creator>Suneja, Arun</creator><creator>Loui, Henning Jakob</creator><creator>Schneider, Christoph</creator><general>Wiley Subscription Services, Inc</general><general>John Wiley and Sons Inc</general><scope>24P</scope><scope>WIN</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7TM</scope><scope>K9.</scope><scope>7X8</scope><scope>5PM</scope><orcidid>https://orcid.org/0000-0001-7392-9556</orcidid></search><sort><creationdate>20200327</creationdate><title>Cooperative Catalysis for the Highly Diastereo‐ and Enantioselective [4+3]‐Cycloannulation of ortho‐Quinone Methides and Carbonyl Ylides</title><author>Suneja, Arun ; Loui, Henning Jakob ; Schneider, Christoph</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c5713-9927a88458ae51dca2af892ce954171d3308155cc949ce672fe3f02008d0e01c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>asymmetric synthesis</topic><topic>Carbonyl compounds</topic><topic>carbonyl ylides</topic><topic>Carbonyls</topic><topic>Catalysis</topic><topic>Communication</topic><topic>Communications</topic><topic>cooperative catalysis</topic><topic>cycloannulation</topic><topic>Enantiomers</topic><topic>Intermediates</topic><topic>ortho-quinone methides</topic><topic>Phosphoric acid</topic><topic>Quinones</topic><topic>Rhodium</topic><topic>Stereoselectivity</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Suneja, Arun</creatorcontrib><creatorcontrib>Loui, Henning Jakob</creatorcontrib><creatorcontrib>Schneider, Christoph</creatorcontrib><collection>Wiley-Blackwell Open Access Titles</collection><collection>Wiley Free Content</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Nucleic Acids Abstracts</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Angewandte Chemie International Edition</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Suneja, Arun</au><au>Loui, Henning Jakob</au><au>Schneider, Christoph</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Cooperative Catalysis for the Highly Diastereo‐ and Enantioselective [4+3]‐Cycloannulation of ortho‐Quinone Methides and Carbonyl Ylides</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew Chem Int Ed Engl</addtitle><date>2020-03-27</date><risdate>2020</risdate><volume>59</volume><issue>14</issue><spage>5536</spage><epage>5540</epage><pages>5536-5540</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><abstract>We describe herein a highly diastereo‐ and enantioselective [4+3]‐cycloannulation of ortho‐quinone methides and carbonyl ylides to furnish functionalized oxa‐bridged dibenzooxacines with excellent yields and stereoselectivity in a single synthetic step. The combination of rhodium and chiral phosphoric acid catalysis working in concert to generate both transient intermediates in situ provides direct access to complex bicyclic products with two quaternary and one tertiary stereogenic centers. The products may be further functionalized into valuable and enantiomerically highly enriched building blocks.
It takes two: A combination of Rh2(OAc)4 and a chiral phosphoric acid catalyzes the in situ generation of transient carbonyl ylides and chiral hydrogen‐bonded ortho‐quinone methides through cooperative catalytic cycles. These transient species then undergo a highly diastereo‐ and enantioselective cycloannulation to afford a broad range of functionalized oxa‐bridged dibenzooxacines featuring two quaternary and one tertiary stereogenic centers.</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>31895488</pmid><doi>10.1002/anie.201913603</doi><tpages>5</tpages><edition>International ed. in English</edition><orcidid>https://orcid.org/0000-0001-7392-9556</orcidid><oa>free_for_read</oa></addata></record> |
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| subjects | asymmetric synthesis Carbonyl compounds carbonyl ylides Carbonyls Catalysis Communication Communications cooperative catalysis cycloannulation Enantiomers Intermediates ortho-quinone methides Phosphoric acid Quinones Rhodium Stereoselectivity |
| title | Cooperative Catalysis for the Highly Diastereo‐ and Enantioselective [4+3]‐Cycloannulation of ortho‐Quinone Methides and Carbonyl Ylides |
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