Diastereoselective dearomative cycloaddition of bicyclobutanes with pyridinium ylides: a modular approach to multisubstituted azabicyclo[3.1.1]heptanes
Diastereoselective (3+3) cycloaddition between bicyclobutanes and pyridinium ylides forms azabicyclo[3.1.1]heptanes via pyridine dearomatization. These reactions proceed under ambient conditions with no need for photochemistry or catalysis, and tolerate a wide range of functional gorups. The resulti...
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| Veröffentlicht in: | Chemical communications (Cambridge, England) England), 2024-11, Vol.6 (89), p.138-1311 |
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| creator | Dhake, Kushal Woelk, Kyla J Krueckl, Liam D. N Alberts, Faith Mutter, James Pohl, Matthew O Thomas, Gilian T Sharma, Muskan Bjornerud-Brown, Jaelyn Fernández, Nahiane Pipaón Schley, Nathan D Leitch, David C |
| description | Diastereoselective (3+3) cycloaddition between bicyclobutanes and pyridinium ylides forms azabicyclo[3.1.1]heptanes
via
pyridine dearomatization. These reactions proceed under ambient conditions with no need for photochemistry or catalysis, and tolerate a wide range of functional gorups. The resulting multicyclic ring systems have diverse synthetic handles for further transformations, making them potentially valuable for the design of Csp
3
-rich drug candidates. These include semi-reduction of the dihydropyridine, and diastereoselective photochemical skeletal rearrangement to give a tetrasubstituted cyclobutane.
Structurally-dense and stereochemically-defined tricyclic heterocycles are easily accessed by (3+3) cycloaddition, leading to versatile Csp
3
-rich scaffolds. |
| doi_str_mv | 10.1039/d4cc04730c |
| format | Article |
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via
pyridine dearomatization. These reactions proceed under ambient conditions with no need for photochemistry or catalysis, and tolerate a wide range of functional gorups. The resulting multicyclic ring systems have diverse synthetic handles for further transformations, making them potentially valuable for the design of Csp
3
-rich drug candidates. These include semi-reduction of the dihydropyridine, and diastereoselective photochemical skeletal rearrangement to give a tetrasubstituted cyclobutane.
Structurally-dense and stereochemically-defined tricyclic heterocycles are easily accessed by (3+3) cycloaddition, leading to versatile Csp
3
-rich scaffolds.</description><identifier>ISSN: 1359-7345</identifier><identifier>EISSN: 1364-548X</identifier><identifier>DOI: 10.1039/d4cc04730c</identifier><identifier>PMID: 39403040</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Cycloaddition ; Cyclobutane ; Heptanes ; Photochemistry ; Stereoselectivity</subject><ispartof>Chemical communications (Cambridge, England), 2024-11, Vol.6 (89), p.138-1311</ispartof><rights>Copyright Royal Society of Chemistry 2024</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c193t-f484b2fbf7733928b50ec91cf659e00d2b26e46772e3db7329b5f1157c3d036f3</cites><orcidid>0000-0002-1468-2714 ; 0000-0002-1539-6031 ; 0000-0002-8726-3318</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/39403040$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Dhake, Kushal</creatorcontrib><creatorcontrib>Woelk, Kyla J</creatorcontrib><creatorcontrib>Krueckl, Liam D. N</creatorcontrib><creatorcontrib>Alberts, Faith</creatorcontrib><creatorcontrib>Mutter, James</creatorcontrib><creatorcontrib>Pohl, Matthew O</creatorcontrib><creatorcontrib>Thomas, Gilian T</creatorcontrib><creatorcontrib>Sharma, Muskan</creatorcontrib><creatorcontrib>Bjornerud-Brown, Jaelyn</creatorcontrib><creatorcontrib>Fernández, Nahiane Pipaón</creatorcontrib><creatorcontrib>Schley, Nathan D</creatorcontrib><creatorcontrib>Leitch, David C</creatorcontrib><title>Diastereoselective dearomative cycloaddition of bicyclobutanes with pyridinium ylides: a modular approach to multisubstituted azabicyclo[3.1.1]heptanes</title><title>Chemical communications (Cambridge, England)</title><addtitle>Chem Commun (Camb)</addtitle><description>Diastereoselective (3+3) cycloaddition between bicyclobutanes and pyridinium ylides forms azabicyclo[3.1.1]heptanes
via
pyridine dearomatization. These reactions proceed under ambient conditions with no need for photochemistry or catalysis, and tolerate a wide range of functional gorups. The resulting multicyclic ring systems have diverse synthetic handles for further transformations, making them potentially valuable for the design of Csp
3
-rich drug candidates. These include semi-reduction of the dihydropyridine, and diastereoselective photochemical skeletal rearrangement to give a tetrasubstituted cyclobutane.
Structurally-dense and stereochemically-defined tricyclic heterocycles are easily accessed by (3+3) cycloaddition, leading to versatile Csp
3
-rich scaffolds.</description><subject>Cycloaddition</subject><subject>Cyclobutane</subject><subject>Heptanes</subject><subject>Photochemistry</subject><subject>Stereoselectivity</subject><issn>1359-7345</issn><issn>1364-548X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><recordid>eNpFkU1r3DAQhkVpaT4vvTcIeit4I1mSte6tOE1bCOSSQKEEo48Rq2CvHH20bP9I_m6c3W0ylxlmHt4Z5kXoAyULSlh7brkxhEtGzBt0SFnDK8GXv94-16KtJOPiAB2ldE_moGL5Hh2wlhNGODlEjxdepQwRQoIBTPZ_AFtQMYxqW5uNGYKy1mcf1jg4rP22pUtWa0j4r88rPG2it37ty4g3g7eQvmCFx2DLoCJW0xSDMiucAx7LkH0qOmWfSwaL1T-1F_zNFnRB71YwbYVP0DunhgSn-3yMbi-_3XQ_qqvr7z-7r1eVoS3LleNLrmunnZSMtfVSCwKmpcY1ogVCbK3rBngjZQ3MasnqVgtHqZCGWcIax47Rp53ufORDgZT7-1Diel7ZM1pzIoWUYqY-7ygTQ0oRXD9FP6q46Snpnz3oL3jXbT3oZvhsL1n0CPYF_f_0Gfi4A2IyL9NXE9kTtISPKA</recordid><startdate>20241105</startdate><enddate>20241105</enddate><creator>Dhake, Kushal</creator><creator>Woelk, Kyla J</creator><creator>Krueckl, Liam D. N</creator><creator>Alberts, Faith</creator><creator>Mutter, James</creator><creator>Pohl, Matthew O</creator><creator>Thomas, Gilian T</creator><creator>Sharma, Muskan</creator><creator>Bjornerud-Brown, Jaelyn</creator><creator>Fernández, Nahiane Pipaón</creator><creator>Schley, Nathan D</creator><creator>Leitch, David C</creator><general>Royal Society of Chemistry</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope><orcidid>https://orcid.org/0000-0002-1468-2714</orcidid><orcidid>https://orcid.org/0000-0002-1539-6031</orcidid><orcidid>https://orcid.org/0000-0002-8726-3318</orcidid></search><sort><creationdate>20241105</creationdate><title>Diastereoselective dearomative cycloaddition of bicyclobutanes with pyridinium ylides: a modular approach to multisubstituted azabicyclo[3.1.1]heptanes</title><author>Dhake, Kushal ; Woelk, Kyla J ; Krueckl, Liam D. N ; Alberts, Faith ; Mutter, James ; Pohl, Matthew O ; Thomas, Gilian T ; Sharma, Muskan ; Bjornerud-Brown, Jaelyn ; Fernández, Nahiane Pipaón ; Schley, Nathan D ; Leitch, David C</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c193t-f484b2fbf7733928b50ec91cf659e00d2b26e46772e3db7329b5f1157c3d036f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><topic>Cycloaddition</topic><topic>Cyclobutane</topic><topic>Heptanes</topic><topic>Photochemistry</topic><topic>Stereoselectivity</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Dhake, Kushal</creatorcontrib><creatorcontrib>Woelk, Kyla J</creatorcontrib><creatorcontrib>Krueckl, Liam D. N</creatorcontrib><creatorcontrib>Alberts, Faith</creatorcontrib><creatorcontrib>Mutter, James</creatorcontrib><creatorcontrib>Pohl, Matthew O</creatorcontrib><creatorcontrib>Thomas, Gilian T</creatorcontrib><creatorcontrib>Sharma, Muskan</creatorcontrib><creatorcontrib>Bjornerud-Brown, Jaelyn</creatorcontrib><creatorcontrib>Fernández, Nahiane Pipaón</creatorcontrib><creatorcontrib>Schley, Nathan D</creatorcontrib><creatorcontrib>Leitch, David C</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Chemical communications (Cambridge, England)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Dhake, Kushal</au><au>Woelk, Kyla J</au><au>Krueckl, Liam D. N</au><au>Alberts, Faith</au><au>Mutter, James</au><au>Pohl, Matthew O</au><au>Thomas, Gilian T</au><au>Sharma, Muskan</au><au>Bjornerud-Brown, Jaelyn</au><au>Fernández, Nahiane Pipaón</au><au>Schley, Nathan D</au><au>Leitch, David C</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Diastereoselective dearomative cycloaddition of bicyclobutanes with pyridinium ylides: a modular approach to multisubstituted azabicyclo[3.1.1]heptanes</atitle><jtitle>Chemical communications (Cambridge, England)</jtitle><addtitle>Chem Commun (Camb)</addtitle><date>2024-11-05</date><risdate>2024</risdate><volume>6</volume><issue>89</issue><spage>138</spage><epage>1311</epage><pages>138-1311</pages><issn>1359-7345</issn><eissn>1364-548X</eissn><abstract>Diastereoselective (3+3) cycloaddition between bicyclobutanes and pyridinium ylides forms azabicyclo[3.1.1]heptanes
via
pyridine dearomatization. These reactions proceed under ambient conditions with no need for photochemistry or catalysis, and tolerate a wide range of functional gorups. The resulting multicyclic ring systems have diverse synthetic handles for further transformations, making them potentially valuable for the design of Csp
3
-rich drug candidates. These include semi-reduction of the dihydropyridine, and diastereoselective photochemical skeletal rearrangement to give a tetrasubstituted cyclobutane.
Structurally-dense and stereochemically-defined tricyclic heterocycles are easily accessed by (3+3) cycloaddition, leading to versatile Csp
3
-rich scaffolds.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>39403040</pmid><doi>10.1039/d4cc04730c</doi><tpages>4</tpages><orcidid>https://orcid.org/0000-0002-1468-2714</orcidid><orcidid>https://orcid.org/0000-0002-1539-6031</orcidid><orcidid>https://orcid.org/0000-0002-8726-3318</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1359-7345 |
| ispartof | Chemical communications (Cambridge, England), 2024-11, Vol.6 (89), p.138-1311 |
| issn | 1359-7345 1364-548X |
| language | eng |
| recordid | cdi_pubmed_primary_39403040 |
| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Cycloaddition Cyclobutane Heptanes Photochemistry Stereoselectivity |
| title | Diastereoselective dearomative cycloaddition of bicyclobutanes with pyridinium ylides: a modular approach to multisubstituted azabicyclo[3.1.1]heptanes |
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