Chiral Symmetry Breaking of Spiropyrans and Spirooxazines by Dynamic Enantioselective Crystallization
Dynamic enantioselective crystallization enabled the chiral symmetry breaking of two spiropyrans and one spirooxazine. The three spiro compounds afforded racemic conglomerate crystals, and easily racemized in alcoholic solution without irradiation. Optically pure enantiomorphic crystals were obtaine...
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| Veröffentlicht in: | Chemistry : a European journal 2019-07, Vol.25 (41), p.9758-9763 |
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| container_issue | 41 |
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| container_title | Chemistry : a European journal |
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| creator | Ishikawa, Hiroki Uemura, Naohiro Saito, Rei Yoshida, Yasushi Mino, Takashi Kasashima, Yoshio Sakamoto, Masami |
| description | Dynamic enantioselective crystallization enabled the chiral symmetry breaking of two spiropyrans and one spirooxazine. The three spiro compounds afforded racemic conglomerate crystals, and easily racemized in alcoholic solution without irradiation. Optically pure enantiomorphic crystals were obtained by vapor‐diffusion crystallization or attrition‐enhanced deracemization (Viedma ripening). Their absolute configurations were determined by single‐crystal X‐ray analysis and each enantiomorphic crystal was correlated with its solid‐state circular dichroism (CD) spectrum.
Spiro‐pure enantiomers: Chiral symmetry breaking of two spiropyrans and one spirooxazine was performed by dynamic enantioselective crystallization. The three spiro compounds afforded racemic conglomerate crystals, and easily racemized in methanol without irradiation. Vapor‐diffusion crystallization or attrition‐enhanced deracemization (Viedma ripening) gave optically pure enantiomorphic crystals. |
| doi_str_mv | 10.1002/chem.201901889 |
| format | Article |
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Spiro‐pure enantiomers: Chiral symmetry breaking of two spiropyrans and one spirooxazine was performed by dynamic enantioselective crystallization. The three spiro compounds afforded racemic conglomerate crystals, and easily racemized in methanol without irradiation. Vapor‐diffusion crystallization or attrition‐enhanced deracemization (Viedma ripening) gave optically pure enantiomorphic crystals.</description><identifier>ISSN: 0947-6539</identifier><identifier>EISSN: 1521-3765</identifier><identifier>DOI: 10.1002/chem.201901889</identifier><identifier>PMID: 31063242</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>Broken symmetry ; Chemistry ; chiral symmetry breaking ; Circular dichroism ; Crystallization ; Crystals ; deracemization ; Dichroism ; dynamic crystallization ; Enantiomers ; Irradiation ; Ripening ; Spiro compounds ; Spirooxazine ; spirooxazines ; Spiropyrans</subject><ispartof>Chemistry : a European journal, 2019-07, Vol.25 (41), p.9758-9763</ispartof><rights>2019 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4769-b9b6e63e2d489de17b489632dd4ca99d53d32019a038db4d58b935c1965693f3</citedby><cites>FETCH-LOGICAL-c4769-b9b6e63e2d489de17b489632dd4ca99d53d32019a038db4d58b935c1965693f3</cites><orcidid>0000-0003-1588-1202 ; 0000-0002-3498-3696 ; 0000-0001-9489-2641</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%2Fchem.201901889$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fchem.201901889$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/31063242$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Ishikawa, Hiroki</creatorcontrib><creatorcontrib>Uemura, Naohiro</creatorcontrib><creatorcontrib>Saito, Rei</creatorcontrib><creatorcontrib>Yoshida, Yasushi</creatorcontrib><creatorcontrib>Mino, Takashi</creatorcontrib><creatorcontrib>Kasashima, Yoshio</creatorcontrib><creatorcontrib>Sakamoto, Masami</creatorcontrib><title>Chiral Symmetry Breaking of Spiropyrans and Spirooxazines by Dynamic Enantioselective Crystallization</title><title>Chemistry : a European journal</title><addtitle>Chemistry</addtitle><description>Dynamic enantioselective crystallization enabled the chiral symmetry breaking of two spiropyrans and one spirooxazine. The three spiro compounds afforded racemic conglomerate crystals, and easily racemized in alcoholic solution without irradiation. Optically pure enantiomorphic crystals were obtained by vapor‐diffusion crystallization or attrition‐enhanced deracemization (Viedma ripening). Their absolute configurations were determined by single‐crystal X‐ray analysis and each enantiomorphic crystal was correlated with its solid‐state circular dichroism (CD) spectrum.
Spiro‐pure enantiomers: Chiral symmetry breaking of two spiropyrans and one spirooxazine was performed by dynamic enantioselective crystallization. The three spiro compounds afforded racemic conglomerate crystals, and easily racemized in methanol without irradiation. Vapor‐diffusion crystallization or attrition‐enhanced deracemization (Viedma ripening) gave optically pure enantiomorphic crystals.</description><subject>Broken symmetry</subject><subject>Chemistry</subject><subject>chiral symmetry breaking</subject><subject>Circular dichroism</subject><subject>Crystallization</subject><subject>Crystals</subject><subject>deracemization</subject><subject>Dichroism</subject><subject>dynamic crystallization</subject><subject>Enantiomers</subject><subject>Irradiation</subject><subject>Ripening</subject><subject>Spiro compounds</subject><subject>Spirooxazine</subject><subject>spirooxazines</subject><subject>Spiropyrans</subject><issn>0947-6539</issn><issn>1521-3765</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNqFkDFv2zAQhYkiReOmXTMGBLJ0kUvyJEocE8VpCqToYO8CJZ5rOhLlkHJS5deHhh0X6JLp4Q7fPbx7hJxzNuWMie_NCrupYFwxXhTqA5nwTPAEcpmdkAlTaZ7IDNQp-RzCmjGmJMAncgqcSRCpmBAsV9brls7HrsPBj_Tao36w7g_tl3S-sb7fjF67QLUz-7n_q1-sw0Drkd6MTne2oTOn3WD7gC02g31CWvoxDLpt7YuOe_eFfFzqNuDXg56Rxe1sUd4l979__Cyv7pMmzaVKalVLlIDCpIUyyPM6agxqTNpopUwGBna_agaFqVOTFbWCrOFKZlLBEs7It73txvePWwxD1dnQYNtqh_02VEKA4AB5oSJ6-R-67rfexXCRklmMA8AiNd1Tje9D8LisNt522o8VZ9Wu_2rXf3XsPx5cHGy3dYfmiL8VHgG1B55ti-M7dlV5N_v1z_wVJiqSfA</recordid><startdate>20190722</startdate><enddate>20190722</enddate><creator>Ishikawa, Hiroki</creator><creator>Uemura, Naohiro</creator><creator>Saito, Rei</creator><creator>Yoshida, Yasushi</creator><creator>Mino, Takashi</creator><creator>Kasashima, Yoshio</creator><creator>Sakamoto, Masami</creator><general>Wiley Subscription Services, Inc</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>K9.</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0003-1588-1202</orcidid><orcidid>https://orcid.org/0000-0002-3498-3696</orcidid><orcidid>https://orcid.org/0000-0001-9489-2641</orcidid></search><sort><creationdate>20190722</creationdate><title>Chiral Symmetry Breaking of Spiropyrans and Spirooxazines by Dynamic Enantioselective Crystallization</title><author>Ishikawa, Hiroki ; Uemura, Naohiro ; Saito, Rei ; Yoshida, Yasushi ; Mino, Takashi ; Kasashima, Yoshio ; Sakamoto, Masami</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4769-b9b6e63e2d489de17b489632dd4ca99d53d32019a038db4d58b935c1965693f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Broken symmetry</topic><topic>Chemistry</topic><topic>chiral symmetry breaking</topic><topic>Circular dichroism</topic><topic>Crystallization</topic><topic>Crystals</topic><topic>deracemization</topic><topic>Dichroism</topic><topic>dynamic crystallization</topic><topic>Enantiomers</topic><topic>Irradiation</topic><topic>Ripening</topic><topic>Spiro compounds</topic><topic>Spirooxazine</topic><topic>spirooxazines</topic><topic>Spiropyrans</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ishikawa, Hiroki</creatorcontrib><creatorcontrib>Uemura, Naohiro</creatorcontrib><creatorcontrib>Saito, Rei</creatorcontrib><creatorcontrib>Yoshida, Yasushi</creatorcontrib><creatorcontrib>Mino, Takashi</creatorcontrib><creatorcontrib>Kasashima, Yoshio</creatorcontrib><creatorcontrib>Sakamoto, Masami</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Chemistry : a European journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ishikawa, Hiroki</au><au>Uemura, Naohiro</au><au>Saito, Rei</au><au>Yoshida, Yasushi</au><au>Mino, Takashi</au><au>Kasashima, Yoshio</au><au>Sakamoto, Masami</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Chiral Symmetry Breaking of Spiropyrans and Spirooxazines by Dynamic Enantioselective Crystallization</atitle><jtitle>Chemistry : a European journal</jtitle><addtitle>Chemistry</addtitle><date>2019-07-22</date><risdate>2019</risdate><volume>25</volume><issue>41</issue><spage>9758</spage><epage>9763</epage><pages>9758-9763</pages><issn>0947-6539</issn><eissn>1521-3765</eissn><abstract>Dynamic enantioselective crystallization enabled the chiral symmetry breaking of two spiropyrans and one spirooxazine. The three spiro compounds afforded racemic conglomerate crystals, and easily racemized in alcoholic solution without irradiation. Optically pure enantiomorphic crystals were obtained by vapor‐diffusion crystallization or attrition‐enhanced deracemization (Viedma ripening). Their absolute configurations were determined by single‐crystal X‐ray analysis and each enantiomorphic crystal was correlated with its solid‐state circular dichroism (CD) spectrum.
Spiro‐pure enantiomers: Chiral symmetry breaking of two spiropyrans and one spirooxazine was performed by dynamic enantioselective crystallization. The three spiro compounds afforded racemic conglomerate crystals, and easily racemized in methanol without irradiation. Vapor‐diffusion crystallization or attrition‐enhanced deracemization (Viedma ripening) gave optically pure enantiomorphic crystals.</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>31063242</pmid><doi>10.1002/chem.201901889</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0003-1588-1202</orcidid><orcidid>https://orcid.org/0000-0002-3498-3696</orcidid><orcidid>https://orcid.org/0000-0001-9489-2641</orcidid></addata></record> |
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| subjects | Broken symmetry Chemistry chiral symmetry breaking Circular dichroism Crystallization Crystals deracemization Dichroism dynamic crystallization Enantiomers Irradiation Ripening Spiro compounds Spirooxazine spirooxazines Spiropyrans |
| title | Chiral Symmetry Breaking of Spiropyrans and Spirooxazines by Dynamic Enantioselective Crystallization |
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