{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,13]],"date-time":"2025-10-13T00:48:50Z","timestamp":1760316530330,"version":"build-2065373602"},"reference-count":113,"publisher":"Wiley","issue":"17","license":[{"start":{"date-parts":[[2010,4,6]],"date-time":"2010-04-06T00:00:00Z","timestamp":1270512000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2010,5,3]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Solvent\u2010dependent, self\u2010discrimination of diamides is described. Mixing a solution of (<jats:italic>R<\/jats:italic>)\u2010<jats:bold>1\u2009a<\/jats:bold> and (<jats:italic>S<\/jats:italic>)\u2010<jats:bold>1\u2009a<\/jats:bold>, which are valine\u2010derived, bis(2\u2010hydroxyphenyl)diamide\u2010bearing, multiple hydrogen\u2010bonding modules, in dichloromethane immediately led to the formation of a thick suspension comprising a 1:1 heterochiral aggregate of <jats:bold>1\u2009a<\/jats:bold>. The solubility of heterochiral <jats:bold>1\u2009a<\/jats:bold> was substantially lower in halogenated solvents than in ethyl acetate. A perusal of racemic crystal structures obtained from chloroform and ethyl acetate revealed a significant difference in the crystal\u2010packing pattern, which is likely to be the basis for the pronounced difference in solubility. Specific self\u2010discrimination of <jats:bold>1\u2009a<\/jats:bold> in an ensemble of eight structurally related molecules showcased the specific aggregation through the hydrogen\u2010bonding network of the bis(2\u2010hydroxyphenyl)diamide framework. The low solubility of heterochiral <jats:bold>1\u2009a<\/jats:bold> in halogenated solvent was exploited to achieve high stereoselectivity in a catalytic asymmetric reaction by using a low enantiomeric excess sample of <jats:bold>1\u2009a<\/jats:bold>.<\/jats:p>","DOI":"10.1002\/chem.201000321","type":"journal-article","created":{"date-parts":[[2010,4,6]],"date-time":"2010-04-06T22:31:01Z","timestamp":1270593061000},"page":"5036-5042","source":"Crossref","is-referenced-by-count":31,"title":["Solvent\u2010Dependent Self\u2010Discrimination of Bis(2\u2010hydroxyphenyl)diamides"],"prefix":"10.1002","volume":"16","author":[{"given":"Akinobu","family":"Matsuzawa","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Akihiro","family":"Nojiri","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Naoya","family":"Kumagai","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Masakatsu","family":"Shibasaki","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2010,4,23]]},"reference":[{"key":"e_1_2_6_1_2","unstructured":"For reviews 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catalysis see:"},{"key":"e_1_2_6_76_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0752585"},{"key":"e_1_2_6_77_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja800326d"},{"key":"e_1_2_6_78_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol8008446"},{"key":"e_1_2_6_79_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja900084k"},{"key":"e_1_2_6_80_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja9052653"},{"key":"e_1_2_6_81_2","unstructured":"See the Supporting Information and Experimental Section for details."},{"key":"e_1_2_6_82_2","unstructured":"CCDC\u2010752886 (rac\u20101\u2009afrom CHCl3) and 752887 (rac\u20101\u2009afrom AcOEt\/n\u2010pentane) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre viawww.ccdc.cam.ac.uk\/data_request\/cif. Summary of crystallographic analysis and crystal structures of optically pure1\u2009afrom CH2Cl2and AcOEt\/n\u2010pentane are provided in the Supporting Information."},{"key":"e_1_2_6_83_2","unstructured":"In reference\u2005[8b] the authors provided a crystal structure of racemic proline incorporating a CHCl3molecule and proposed that this incorporation caused a significant enhancement of the eutecticeevalue. For a more detailed study on the tuning of eutectic composition by achiral additives see reference\u2005[8e]."},{"key":"e_1_2_6_84_2","unstructured":"The amount of (S)\u20101\u2009b (S)\u20101\u2009c (S)\u20101\u2009d (S)\u20101\u2009e (S)\u20101\u2009f and (S)\u20101\u2009gin the filtrate remained almost identical to the initial concentration whereas the amount of (S)\u20101\u2009aand (R)\u20101\u2009awas significantly decreased. A small imbalance of the amount of (S)\u20101\u2009aand (R)\u20101\u2009ain the filtered insoluble material indicated that tiny amounts of (R)\u20101\u2009a\/(S)\u20101\u2009b\u2013gaggregates were formed."},{"key":"e_1_2_6_85_2","unstructured":"Similar experiments were performed previously see references\u2005[8b] and [9]."},{"key":"e_1_2_6_86_2","unstructured":"For recent reviews on direct Mannich reactions using unmodified pronucleophiles see:"},{"key":"e_1_2_6_87_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.200700409"},{"key":"e_1_2_6_88_2","first-page":"143","volume-title":"Comprehensive Asymmetric Catalysis","author":"Kobayashi S.","year":"2003"},{"key":"e_1_2_6_89_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2006.11.076"},{"key":"e_1_2_6_90_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr0684016"},{"key":"e_1_2_6_90_3","doi-asserted-by":"publisher","DOI":"10.1021\/cr0684016"},{"key":"e_1_2_6_91_2","unstructured":"For recent reviews for electrophilic amination of carbonyl compounds see:"},{"key":"e_1_2_6_92_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200390228"},{"key":"e_1_2_6_92_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200390283"},{"key":"e_1_2_6_93_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.200300657"},{"key":"e_1_2_6_94_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200462314"},{"key":"e_1_2_6_94_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200462314"},{"key":"e_1_2_6_95_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetasy.2009.01.002"}],"container-title":["Chemistry \u2013 A European Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fchem.201000321","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.201000321","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T16:45:50Z","timestamp":1760287550000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/chem.201000321"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2010,4,23]]},"references-count":113,"journal-issue":{"issue":"17","published-print":{"date-parts":[[2010,5,3]]}},"alternative-id":["10.1002\/chem.201000321"],"URL":"https:\/\/doi.org\/10.1002\/chem.201000321","archive":["Portico"],"relation":{},"ISSN":["0947-6539","1521-3765"],"issn-type":[{"type":"print","value":"0947-6539"},{"type":"electronic","value":"1521-3765"}],"subject":[],"published":{"date-parts":[[2010,4,23]]}}}