Construction of thioglycoside bonds via an asymmetric organocatalyzed sulfa-Michael/aldol reaction: access to 4'-thionucleosides
Thioglycoside bond formation an asymmetric sulfa-Michael/aldol reaction of ( )-β-nucleobase acrylketones and 1,4-dithiane-2,5-diol has been achieved with a cinchona alkaloid-derived bifunctional squaramide chiral catalyst. Diverse purine, benzimidazole, and imidazole substrates are well tolerated an...
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| Veröffentlicht in: | Chemical communications (Cambridge, England) England), 2024-05, Vol.60 (38), p.5018-5021 |
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| container_title | Chemical communications (Cambridge, England) |
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| creator | Wei, Tao Xie, Ming-Sheng Guo, Hai-Ming |
| description | Thioglycoside bond formation
an asymmetric sulfa-Michael/aldol reaction of (
)-β-nucleobase acrylketones and 1,4-dithiane-2,5-diol has been achieved with a cinchona alkaloid-derived bifunctional squaramide chiral catalyst. Diverse purine, benzimidazole, and imidazole substrates are well tolerated and generate 4'-thionucleoside derivatives containing three contiguous stereogenic centers with excellent results (30 examples, up to 97% yield, >20 : 1 dr and up to 99% ee). Moreover, the novel strategy provides an efficient and convenient synthetic route to construct chiral 4'-thionucleosides. |
| doi_str_mv | 10.1039/d4cc00984c |
| format | Article |
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an asymmetric sulfa-Michael/aldol reaction of (
)-β-nucleobase acrylketones and 1,4-dithiane-2,5-diol has been achieved with a cinchona alkaloid-derived bifunctional squaramide chiral catalyst. Diverse purine, benzimidazole, and imidazole substrates are well tolerated and generate 4'-thionucleoside derivatives containing three contiguous stereogenic centers with excellent results (30 examples, up to 97% yield, >20 : 1 dr and up to 99% ee). Moreover, the novel strategy provides an efficient and convenient synthetic route to construct chiral 4'-thionucleosides.</description><identifier>ISSN: 1359-7345</identifier><identifier>EISSN: 1364-548X</identifier><identifier>DOI: 10.1039/d4cc00984c</identifier><identifier>PMID: 38639063</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Aldehydes ; Asymmetry ; Imidazole ; Substrates</subject><ispartof>Chemical communications (Cambridge, England), 2024-05, Vol.60 (38), p.5018-5021</ispartof><rights>Copyright Royal Society of Chemistry 2024</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c274t-5885f2b5485681c0d0adfc48114168f9f805fe179495a981e6068a6bc1dd43093</cites><orcidid>0000-0003-4113-2168 ; 0000-0003-0629-4524</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/38639063$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Wei, Tao</creatorcontrib><creatorcontrib>Xie, Ming-Sheng</creatorcontrib><creatorcontrib>Guo, Hai-Ming</creatorcontrib><title>Construction of thioglycoside bonds via an asymmetric organocatalyzed sulfa-Michael/aldol reaction: access to 4'-thionucleosides</title><title>Chemical communications (Cambridge, England)</title><addtitle>Chem Commun (Camb)</addtitle><description>Thioglycoside bond formation
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an asymmetric sulfa-Michael/aldol reaction of (
)-β-nucleobase acrylketones and 1,4-dithiane-2,5-diol has been achieved with a cinchona alkaloid-derived bifunctional squaramide chiral catalyst. Diverse purine, benzimidazole, and imidazole substrates are well tolerated and generate 4'-thionucleoside derivatives containing three contiguous stereogenic centers with excellent results (30 examples, up to 97% yield, >20 : 1 dr and up to 99% ee). Moreover, the novel strategy provides an efficient and convenient synthetic route to construct chiral 4'-thionucleosides.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>38639063</pmid><doi>10.1039/d4cc00984c</doi><tpages>4</tpages><orcidid>https://orcid.org/0000-0003-4113-2168</orcidid><orcidid>https://orcid.org/0000-0003-0629-4524</orcidid></addata></record> |
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| ispartof | Chemical communications (Cambridge, England), 2024-05, Vol.60 (38), p.5018-5021 |
| issn | 1359-7345 1364-548X |
| language | eng |
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| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Aldehydes Asymmetry Imidazole Substrates |
| title | Construction of thioglycoside bonds via an asymmetric organocatalyzed sulfa-Michael/aldol reaction: access to 4'-thionucleosides |
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