{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,4,3]],"date-time":"2026-04-03T03:31:49Z","timestamp":1775187109095,"version":"3.50.1"},"reference-count":150,"publisher":"Wiley","issue":"7","license":[{"start":{"date-parts":[[2022,7,27]],"date-time":"2022-07-27T00:00:00Z","timestamp":1658880000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["The Chemical Record"],"published-print":{"date-parts":[[2023,7]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>The aldol reaction is one of the most important carbon\u2010carbon bond\u2010forming reactions in organic chemistry. Asymmetric direct cross\u2010aldol reaction of two different aldehydes has been regarded as a difficult reaction because of the side reactions such as self\u2010aldol reaction and over reaction. We found that trifluoromethyl\u2010substituted diarylprolinol, \u03b1,\u03b1\u2010bis[3,5\u2010bis(trifluoromethyl)phenyl]\u20102\u2010pyrrolidinemethanol (<jats:bold>1<\/jats:bold>), is an effective organocatalyst that promotes several cross\u2010aldol reactions of aldehydes with excellent diastereo\u2010 and enantioselectivities. Acetaldehyde can be employed as a suitable nucleophilic aldehyde. Successful electrophilic aldehydes are ethyl glyoxylate, chloroacetaldehyde, dichloroacetaldehyde, chloral, \u03b1\u2010alkyl\u2010\u03b1\u2010oxo aldehyde, trifluoroacetaldehyde, glyoxal, alkenyl aldehyde, alkynyl aldehyde, and formaldehyde. Some of the aldehydes are commercially available as a polymer solution, an aqueous solution, or in the hydrated form. They can be used directly in the asymmetric aldol reaction as a commercially available form, which is a synthetic advantage. Given that the obtained aldol products possess several functional groups along with a formyl moiety, they are synthetically useful chiral building blocks.<\/jats:p>","DOI":"10.1002\/tcr.202200159","type":"journal-article","created":{"date-parts":[[2022,7,28]],"date-time":"2022-07-28T03:14:38Z","timestamp":1658978078000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":7,"title":["Diarylprolinol as an Effective Organocatalyst in Asymmetric Cross\u2010Aldol Reactions of Two Different Aldehydes"],"prefix":"10.1002","volume":"23","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-1838-5389","authenticated-orcid":false,"given":"Yujiro","family":"Hayashi","sequence":"first","affiliation":[{"name":"Department of Chemistry Graduate School of Science Tohoku University  6-3 Aramaki Aza-Aoba, Aoba-ku Sendai Miyagi 980-8578 Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2022,7,27]]},"reference":[{"key":"e_1_2_23_1_1","unstructured":"\u00a0"},{"key":"e_1_2_23_2_2","volume-title":"Modern Aldol Reactions, Vols. 1, 2","author":"Denmark S. E.","year":"2004"},{"key":"e_1_2_23_3_2","doi-asserted-by":"publisher","DOI":"10.1039\/C7CS00824D"},{"key":"e_1_2_23_4_1","unstructured":"\u00a0"},{"key":"e_1_2_23_5_2","unstructured":"Z.\u2005G. Hajos D.\u2005R. Parrish German Patent DE 2102623 1971;"},{"key":"e_1_2_23_6_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00925a003"},{"key":"e_1_2_23_7_1","unstructured":"\u00a0"},{"key":"e_1_2_23_8_2","unstructured":"U. Eder G. Sauer R. Wiechert German Patent DE 2014757 1971;"},{"key":"e_1_2_23_9_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19710831307"},{"key":"e_1_2_23_9_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.197104961"},{"key":"e_1_2_23_10_1","doi-asserted-by":"publisher","DOI":"10.1055\/s-0031-1290107"},{"key":"e_1_2_23_11_1","unstructured":"\u00a0"},{"key":"e_1_2_23_12_2","first-page":"203","volume":"28","author":"Mukaiyama T.","year":"1982","journal-title":"Org. React."},{"key":"e_1_2_23_13_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201303192"},{"key":"e_1_2_23_13_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201303192"},{"key":"e_1_2_23_14_1","unstructured":"\u00a0"},{"key":"e_1_2_23_15_2","doi-asserted-by":"publisher","DOI":"10.1002\/9783527619566.ch14"},{"key":"e_1_2_23_16_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201302084"},{"key":"e_1_2_23_16_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201302084"},{"key":"e_1_2_23_17_1","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19971091716"},{"key":"e_1_2_23_17_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.199718711"},{"key":"e_1_2_23_18_1","unstructured":"\u00a0"},{"key":"e_1_2_23_19_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja003033n"},{"key":"e_1_2_23_20_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja051526s"},{"key":"e_1_2_23_21_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja994280y"},{"key":"e_1_2_23_22_1","unstructured":"Selected books on organocatalysis."},{"key":"e_1_2_23_23_2","volume-title":"Asymmetric Organocatalysis 1, Lewis Base and Acid Catalysts","author":"List B.","year":"2012"},{"key":"e_1_2_23_24_2","volume-title":"Asymmetric Organocatalysis 2, Br\u00f8nsted Base and Acid Catalysts, and Additional Topics","author":"Maruoka K.","year":"2012"},{"key":"e_1_2_23_25_2","volume-title":"Handbook of Reagents for Organic Synthesis, Reagents for Organocatalysis","author":"Rovis T.","year":"2016"},{"key":"e_1_2_23_26_1","unstructured":"\u00a0"},{"key":"e_1_2_23_27_2","first-page":"35","volume-title":"Asymmetric Organocatalysis 1, Lewis Base and Acid catalysts","author":"Yliniemel\u00e4-Sipari S. M.","year":"2012"},{"key":"e_1_2_23_28_2","first-page":"237","volume-title":"Comprehensive Organic Synthesis 2nd Edition, Vol. 2","author":"Mase N.","year":"2014"},{"key":"e_1_2_23_29_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.6b00243"},{"key":"e_1_2_23_30_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.5b11192"},{"key":"e_1_2_23_31_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja0262378"},{"key":"e_1_2_23_32_1","unstructured":"\u00a0"},{"key":"e_1_2_23_33_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200604640"},{"key":"e_1_2_23_33_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200604640"},{"key":"e_1_2_23_34_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200900267"},{"key":"e_1_2_23_35_2","doi-asserted-by":"publisher","DOI":"10.1039\/c1cc14347f"},{"key":"e_1_2_23_36_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja208873k"},{"key":"e_1_2_23_37_2","doi-asserted-by":"publisher","DOI":"10.1039\/c2cc32772d"},{"key":"e_1_2_23_38_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol4036837"},{"key":"e_1_2_23_39_1","unstructured":"\u00a0"},{"key":"e_1_2_23_40_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo202558f"},{"key":"e_1_2_23_41_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja2118392"},{"key":"e_1_2_23_42_1","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200601156"},{"key":"e_1_2_23_42_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200601156"},{"key":"e_1_2_23_43_1","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200704870"},{"key":"e_1_2_23_43_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200704870"},{"key":"e_1_2_23_44_1","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200801408"},{"key":"e_1_2_23_44_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200801408"},{"key":"e_1_2_23_45_1","unstructured":"\u00a0"},{"key":"e_1_2_23_46_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200502488"},{"key":"e_1_2_23_46_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200502488"},{"key":"e_1_2_23_47_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200700363"},{"key":"e_1_2_23_48_1","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200802079"},{"key":"e_1_2_23_48_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200802079"},{"key":"e_1_2_23_49_1","unstructured":"Reviews see;"},{"key":"e_1_2_23_50_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200602943"},{"key":"e_1_2_23_50_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200602943"},{"key":"e_1_2_23_51_2","doi-asserted-by":"publisher","DOI":"10.1002\/asia.200700417"},{"key":"e_1_2_23_52_2","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.200900797"},{"key":"e_1_2_23_53_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar200149w"},{"key":"e_1_2_23_54_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-0031-1290774"},{"key":"e_1_2_23_55_2","first-page":"287","volume-title":"Diarylprolinol Silyl Ethers, Development and Application as Organocatalysts. in Sustainable Catalysis","author":"Gotoh H.","year":"2013"},{"key":"e_1_2_23_56_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201503920"},{"key":"e_1_2_23_56_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201503920"},{"key":"e_1_2_23_57_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.8b00583"},{"key":"e_1_2_23_58_1","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200500599"},{"key":"e_1_2_23_58_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200500599"},{"key":"e_1_2_23_59_1","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200462101"},{"key":"e_1_2_23_59_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200462101"},{"key":"e_1_2_23_60_1","unstructured":"Reviews see;"},{"key":"e_1_2_23_61_2","doi-asserted-by":"publisher","DOI":"10.1039\/b900098d"},{"key":"e_1_2_23_62_2","doi-asserted-by":"publisher","DOI":"10.1039\/c3cc36928e"},{"key":"e_1_2_23_63_2","doi-asserted-by":"publisher","DOI":"10.1002\/cctc.201900569"},{"key":"e_1_2_23_64_1","unstructured":"\u00a0"},{"key":"e_1_2_23_65_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00252a056"},{"key":"e_1_2_23_66_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00259a075"},{"key":"e_1_2_23_67_1","unstructured":"\u00a0"},{"key":"e_1_2_23_68_2","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3757(20020517)114:10<1724::AID-ANGE1724>3.0.CO;2-Q"},{"key":"e_1_2_23_68_3","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3773(20020517)41:10<1650::AID-ANIE1650>3.0.CO;2-B"},{"key":"e_1_2_23_69_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200805374"},{"key":"e_1_2_23_69_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200805374"},{"key":"e_1_2_23_70_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja0616433"},{"key":"e_1_2_23_71_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol050694m"},{"key":"e_1_2_23_72_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo015881m"},{"key":"e_1_2_23_73_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol802438u"},{"key":"e_1_2_23_74_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol901432a"},{"key":"e_1_2_23_75_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol1009812"},{"key":"e_1_2_23_76_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.oprd.6b00178"},{"key":"e_1_2_23_77_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0960-894X(98)00098-5"},{"key":"e_1_2_23_78_1","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200603378"},{"key":"e_1_2_23_78_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200603378"},{"key":"e_1_2_23_79_1","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201005577"},{"key":"e_1_2_23_79_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201005577"},{"key":"e_1_2_23_80_1","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.201501111"},{"key":"e_1_2_23_81_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)92655-8"},{"key":"e_1_2_23_82_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja00031a069"},{"key":"e_1_2_23_83_1","unstructured":"\u00a0"},{"key":"e_1_2_23_84_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-1994-25457"},{"key":"e_1_2_23_85_2","doi-asserted-by":"publisher","DOI":"10.1016\/0957-4166(95)00415-7"},{"key":"e_1_2_23_86_1","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200352724"},{"key":"e_1_2_23_86_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200352724"},{"key":"e_1_2_23_87_1","first-page":"1703","author":"Zhang F.","year":"2006","journal-title":"Synlett"},{"key":"e_1_2_23_88_1","doi-asserted-by":"publisher","DOI":"10.1002\/cctc.201500282"},{"key":"e_1_2_23_89_1","unstructured":"\u00a0"},{"key":"e_1_2_23_90_2","first-page":"73","author":"Xiong Y.","year":"2008","journal-title":"Synlett"},{"key":"e_1_2_23_91_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200900267"},{"key":"e_1_2_23_92_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200903471"},{"key":"e_1_2_23_93_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmcl.2009.03.128"},{"key":"e_1_2_23_94_1","doi-asserted-by":"publisher","DOI":"10.1039\/c2cc31230a"},{"key":"e_1_2_23_95_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)87969-1"},{"key":"e_1_2_23_96_1","first-page":"3061","author":"Lorenz M.","year":"2009","journal-title":"Synthesis"},{"key":"e_1_2_23_97_1","doi-asserted-by":"publisher","DOI":"10.1016\/0040-4020(95)00858-6"},{"key":"e_1_2_23_98_1","unstructured":"\u00a0"},{"key":"e_1_2_23_99_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-0030-1259543"},{"key":"e_1_2_23_100_2","first-page":"1788","author":"Erratum","year":"2011","journal-title":"Synlett"},{"key":"e_1_2_23_101_1","unstructured":"\u00a0"},{"key":"e_1_2_23_102_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00727a027"},{"key":"e_1_2_23_103_2","doi-asserted-by":"publisher","DOI":"10.1021\/es060810w"},{"key":"e_1_2_23_104_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.saa.2012.09.050"},{"key":"e_1_2_23_105_1","doi-asserted-by":"publisher","DOI":"10.1002\/cctc.201300247"},{"key":"e_1_2_23_106_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja00219a035"},{"key":"e_1_2_23_107_1","doi-asserted-by":"publisher","DOI":"10.1039\/C5CC02438B"},{"key":"e_1_2_23_108_1","doi-asserted-by":"publisher","DOI":"10.1002\/asia.201901236"},{"key":"e_1_2_23_109_1","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1521-3757(19980803)110:15<2092::AID-ANGE2092>3.0.CO;2-M"},{"key":"e_1_2_23_109_2","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1521-3773(19980817)37:15<1986::AID-ANIE1986>3.0.CO;2-Z"},{"key":"e_1_2_23_110_1","volume-title":"Enantioselective Chemical Synthesis","author":"Corey E. J.","year":"2010"},{"key":"e_1_2_23_111_1","doi-asserted-by":"publisher","DOI":"10.1002\/cctc.201300390"},{"key":"e_1_2_23_112_1","doi-asserted-by":"publisher","DOI":"10.1039\/c3sc51027a"},{"key":"e_1_2_23_113_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.6b01524"},{"key":"e_1_2_23_114_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo970057c"},{"key":"e_1_2_23_115_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2004.06.062"},{"key":"e_1_2_23_116_1","unstructured":"\u00a0"},{"key":"e_1_2_23_117_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol9017479"},{"key":"e_1_2_23_118_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.5b00380"},{"key":"e_1_2_23_119_1","doi-asserted-by":"publisher","DOI":"10.1246\/cl.131199"},{"key":"e_1_2_23_120_1","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201500623"},{"key":"e_1_2_23_121_1","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201209380"},{"key":"e_1_2_23_121_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201209380"},{"key":"e_1_2_23_122_1","doi-asserted-by":"publisher","DOI":"10.1246\/cl.130544"},{"key":"e_1_2_23_123_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201705930"},{"key":"e_1_2_23_124_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(97)00781-3"},{"key":"e_1_2_23_125_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.1c01986"},{"key":"e_1_2_23_126_1","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.201500008"},{"key":"e_1_2_23_127_1","doi-asserted-by":"publisher","DOI":"10.1246\/cl.200304"},{"key":"e_1_2_23_128_1","doi-asserted-by":"publisher","DOI":"10.1246\/cl.170034"},{"key":"e_1_2_23_129_1","author":"Hayashi Y.","year":"2022","journal-title":"Adv. Synth. Catal."}],"container-title":["The Chemical Record"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/tcr.202200159","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/tcr.202200159","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/tcr.202200159","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,1,14]],"date-time":"2025-01-14T07:13:11Z","timestamp":1736838791000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/tcr.202200159"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2022,7,27]]},"references-count":150,"journal-issue":{"issue":"7","published-print":{"date-parts":[[2023,7]]}},"alternative-id":["10.1002\/tcr.202200159"],"URL":"https:\/\/doi.org\/10.1002\/tcr.202200159","archive":["Portico"],"relation":{},"ISSN":["1527-8999","1528-0691"],"issn-type":[{"value":"1527-8999","type":"print"},{"value":"1528-0691","type":"electronic"}],"subject":[],"published":{"date-parts":[[2022,7,27]]},"assertion":[{"value":"2022-06-07","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2022-07-07","order":2,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2022-07-27","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e202200159"}}