Achiral 2‐pyridone and 4‐aminopyridine act as chiral inducers of asymmetric autocatalysis with amplification of enantiomeric excess via the formation of chiral crystals
Enantiomorphous crystals of achiral 2‐pyridone and 4‐aminopyridine served as sources of chirality, to induce the asymmetric autocatalysis of 5‐pyrimidyl alkanol during the asymmetric addition of diisopropylzinc to the corresponding pyrimidine‐5‐carbaldehyde, that is, the Soai reaction. Following a s...
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| Veröffentlicht in: | Chirality (New York, N.Y.) N.Y.), 2024-01, Vol.36 (1), p.e23617-n/a |
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| container_title | Chirality (New York, N.Y.) |
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| creator | Matsumoto, Arimasa Tateishi, Daisuke Nakajima, Tsuyoshi Kurosaki, Shiori Ogawa, Tomohiro Kawasaki, Tsuneomi Soai, Kenso |
| description | Enantiomorphous crystals of achiral 2‐pyridone and 4‐aminopyridine served as sources of chirality, to induce the asymmetric autocatalysis of 5‐pyrimidyl alkanol during the asymmetric addition of diisopropylzinc to the corresponding pyrimidine‐5‐carbaldehyde, that is, the Soai reaction. Following a significant amplification of enantiomeric excess through asymmetric autocatalysis, highly enantioenriched 5‐pyrimidyl alkanol could be synthesized with their corresponding absolute configurations to those of chiral crystals of 2‐pyridone and 4‐aminopyridine.
Enantiomorphic crystals of achiral 2‐pyridone and 4‐aminopyridine acted as chiral sources in the Soai reaction, involving the asymmetric addition of diisopropylzinc to pyrimidine‐5‐carbaldehyde. Through asymmetric autocatalysis, the enantioenrichment was significantly amplified, resulting in the formation of highly enantioenriched 5‐pyrimidyl alkanol with absolute configurations corresponding to those of the chiral crystals. |
| doi_str_mv | 10.1002/chir.23617 |
| format | Article |
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Enantiomorphic crystals of achiral 2‐pyridone and 4‐aminopyridine acted as chiral sources in the Soai reaction, involving the asymmetric addition of diisopropylzinc to pyrimidine‐5‐carbaldehyde. Through asymmetric autocatalysis, the enantioenrichment was significantly amplified, resulting in the formation of highly enantioenriched 5‐pyrimidyl alkanol with absolute configurations corresponding to those of the chiral crystals.</description><identifier>ISSN: 0899-0042</identifier><identifier>EISSN: 1520-636X</identifier><identifier>DOI: 10.1002/chir.23617</identifier><identifier>PMID: 37621025</identifier><language>eng</language><publisher>United States</publisher><subject>5‐pyrimidyl alkanol ; aminopyridine ; amplification of ee ; asymmetric autocatalysis ; chiral crystal ; homochirality ; origin of chirality ; pyridone ; pyrimidine‐5‐carbaldehyde ; Soai reaction</subject><ispartof>Chirality (New York, N.Y.), 2024-01, Vol.36 (1), p.e23617-n/a</ispartof><rights>2023 The Authors. published by Wiley Periodicals LLC.</rights><rights>2023 The Authors. Chirality published by Wiley Periodicals LLC.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c3247-47dc8b3461d70819e90ae4c33176721edd98eeebb07c2e397511b32bbaf603eb3</cites><orcidid>0000-0002-6332-2096</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%2Fchir.23617$$EPDF$$P50$$Gwiley$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fchir.23617$$EHTML$$P50$$Gwiley$$Hfree_for_read</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/37621025$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Matsumoto, Arimasa</creatorcontrib><creatorcontrib>Tateishi, Daisuke</creatorcontrib><creatorcontrib>Nakajima, Tsuyoshi</creatorcontrib><creatorcontrib>Kurosaki, Shiori</creatorcontrib><creatorcontrib>Ogawa, Tomohiro</creatorcontrib><creatorcontrib>Kawasaki, Tsuneomi</creatorcontrib><creatorcontrib>Soai, Kenso</creatorcontrib><title>Achiral 2‐pyridone and 4‐aminopyridine act as chiral inducers of asymmetric autocatalysis with amplification of enantiomeric excess via the formation of chiral crystals</title><title>Chirality (New York, N.Y.)</title><addtitle>Chirality</addtitle><description>Enantiomorphous crystals of achiral 2‐pyridone and 4‐aminopyridine served as sources of chirality, to induce the asymmetric autocatalysis of 5‐pyrimidyl alkanol during the asymmetric addition of diisopropylzinc to the corresponding pyrimidine‐5‐carbaldehyde, that is, the Soai reaction. Following a significant amplification of enantiomeric excess through asymmetric autocatalysis, highly enantioenriched 5‐pyrimidyl alkanol could be synthesized with their corresponding absolute configurations to those of chiral crystals of 2‐pyridone and 4‐aminopyridine.
Enantiomorphic crystals of achiral 2‐pyridone and 4‐aminopyridine acted as chiral sources in the Soai reaction, involving the asymmetric addition of diisopropylzinc to pyrimidine‐5‐carbaldehyde. Through asymmetric autocatalysis, the enantioenrichment was significantly amplified, resulting in the formation of highly enantioenriched 5‐pyrimidyl alkanol with absolute configurations corresponding to those of the chiral crystals.</description><subject>5‐pyrimidyl alkanol</subject><subject>aminopyridine</subject><subject>amplification of ee</subject><subject>asymmetric autocatalysis</subject><subject>chiral crystal</subject><subject>homochirality</subject><subject>origin of chirality</subject><subject>pyridone</subject><subject>pyrimidine‐5‐carbaldehyde</subject><subject>Soai reaction</subject><issn>0899-0042</issn><issn>1520-636X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><sourceid>24P</sourceid><sourceid>WIN</sourceid><recordid>eNp9kcFq3DAQhkVJabbbXvIAQcdQcDqSvJZ9DEuaLCwUSgu9GVkeswqWtZHsbHzLI-RB8lR5ksrZzR57muHn-_9h-Ak5Y3DJAPh3vTH-kouMyQ9kxhYckkxkf0_IDPKiSABSfko-h3AHAEUm0k_kVMiMM-CLGXm5mtyqpfz16Xk7elO7DqnqappGQVnTuTfVTKruqQr0YDBdPWj0gbomqqO12HujqRp6p1Wv2jGYQHem31Blt61pTFSN6yYcO9XF3eJkwEeNIdAHo2i_Qdo4b4_g4ZT2Y4iJ4Qv52MSBXw9zTv78uP69vE3WP29Wy6t1ogVPZZLKWueVSDNWS8hZgQUoTLUQTGaSM6zrIkfEqgKpOYpCLhirBK8q1WQgsBJzcrHP3Xp3P2DoS2uCxrZVHbohlDxfyDwFzouIftuj2rsQPDbl1hur_FgyKKd2yumH8q2dCJ8fcofKYn1E3-uIANsDO9Pi-J-ocnm7-rUP_QfZ-KCt</recordid><startdate>202401</startdate><enddate>202401</enddate><creator>Matsumoto, Arimasa</creator><creator>Tateishi, Daisuke</creator><creator>Nakajima, Tsuyoshi</creator><creator>Kurosaki, Shiori</creator><creator>Ogawa, Tomohiro</creator><creator>Kawasaki, Tsuneomi</creator><creator>Soai, Kenso</creator><scope>24P</scope><scope>WIN</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-6332-2096</orcidid></search><sort><creationdate>202401</creationdate><title>Achiral 2‐pyridone and 4‐aminopyridine act as chiral inducers of asymmetric autocatalysis with amplification of enantiomeric excess via the formation of chiral crystals</title><author>Matsumoto, Arimasa ; Tateishi, Daisuke ; Nakajima, Tsuyoshi ; Kurosaki, Shiori ; Ogawa, Tomohiro ; Kawasaki, Tsuneomi ; Soai, Kenso</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3247-47dc8b3461d70819e90ae4c33176721edd98eeebb07c2e397511b32bbaf603eb3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><topic>5‐pyrimidyl alkanol</topic><topic>aminopyridine</topic><topic>amplification of ee</topic><topic>asymmetric autocatalysis</topic><topic>chiral crystal</topic><topic>homochirality</topic><topic>origin of chirality</topic><topic>pyridone</topic><topic>pyrimidine‐5‐carbaldehyde</topic><topic>Soai reaction</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Matsumoto, Arimasa</creatorcontrib><creatorcontrib>Tateishi, Daisuke</creatorcontrib><creatorcontrib>Nakajima, Tsuyoshi</creatorcontrib><creatorcontrib>Kurosaki, Shiori</creatorcontrib><creatorcontrib>Ogawa, Tomohiro</creatorcontrib><creatorcontrib>Kawasaki, Tsuneomi</creatorcontrib><creatorcontrib>Soai, Kenso</creatorcontrib><collection>Wiley-Blackwell Open Access Titles</collection><collection>Wiley Free Content</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Chirality (New York, N.Y.)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Matsumoto, Arimasa</au><au>Tateishi, Daisuke</au><au>Nakajima, Tsuyoshi</au><au>Kurosaki, Shiori</au><au>Ogawa, Tomohiro</au><au>Kawasaki, Tsuneomi</au><au>Soai, Kenso</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Achiral 2‐pyridone and 4‐aminopyridine act as chiral inducers of asymmetric autocatalysis with amplification of enantiomeric excess via the formation of chiral crystals</atitle><jtitle>Chirality (New York, N.Y.)</jtitle><addtitle>Chirality</addtitle><date>2024-01</date><risdate>2024</risdate><volume>36</volume><issue>1</issue><spage>e23617</spage><epage>n/a</epage><pages>e23617-n/a</pages><issn>0899-0042</issn><eissn>1520-636X</eissn><abstract>Enantiomorphous crystals of achiral 2‐pyridone and 4‐aminopyridine served as sources of chirality, to induce the asymmetric autocatalysis of 5‐pyrimidyl alkanol during the asymmetric addition of diisopropylzinc to the corresponding pyrimidine‐5‐carbaldehyde, that is, the Soai reaction. Following a significant amplification of enantiomeric excess through asymmetric autocatalysis, highly enantioenriched 5‐pyrimidyl alkanol could be synthesized with their corresponding absolute configurations to those of chiral crystals of 2‐pyridone and 4‐aminopyridine.
Enantiomorphic crystals of achiral 2‐pyridone and 4‐aminopyridine acted as chiral sources in the Soai reaction, involving the asymmetric addition of diisopropylzinc to pyrimidine‐5‐carbaldehyde. Through asymmetric autocatalysis, the enantioenrichment was significantly amplified, resulting in the formation of highly enantioenriched 5‐pyrimidyl alkanol with absolute configurations corresponding to those of the chiral crystals.</abstract><cop>United States</cop><pmid>37621025</pmid><doi>10.1002/chir.23617</doi><tpages>8</tpages><orcidid>https://orcid.org/0000-0002-6332-2096</orcidid><oa>free_for_read</oa></addata></record> |
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| subjects | 5‐pyrimidyl alkanol aminopyridine amplification of ee asymmetric autocatalysis chiral crystal homochirality origin of chirality pyridone pyrimidine‐5‐carbaldehyde Soai reaction |
| title | Achiral 2‐pyridone and 4‐aminopyridine act as chiral inducers of asymmetric autocatalysis with amplification of enantiomeric excess via the formation of chiral crystals |
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