{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,3,10]],"date-time":"2026-03-10T17:18:45Z","timestamp":1773163125028,"version":"3.50.1"},"reference-count":49,"publisher":"Wiley","issue":"12","license":[{"start":{"date-parts":[[2015,8,17]],"date-time":"2015-08-17T00:00:00Z","timestamp":1439769600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"name":"Grant-in-Aid for Scientific Research (C)","award":["19550104"],"award-info":[{"award-number":["19550104"]}]},{"DOI":"10.13039\/501100001691","name":"Japan Society for the Promotion of Science","doi-asserted-by":"crossref","id":[{"id":"10.13039\/501100001691","id-type":"DOI","asserted-by":"crossref"}]},{"name":"Central Glass Co., Ltd."}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Chemistry \u0097 An Asian Journal"],"published-print":{"date-parts":[[2015,12]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>A direct, concise, and enantioselective synthesis of 2\u2010substituted 4,4,4\u2010trifluorobutane\u20101,3\u2010diols based on the organocatalytic asymmetric direct aldol reaction of an ethyl hemiacetal of trifluoroacetaldehyde with various aldehydes was examined. A catalytic amount (30\u2005mol\u2009%) of commercially available and inexpensive <jats:sc>l<\/jats:sc>\u2010prolinamide is quite effective as an organocatalyst for the catalytic in situ generation of gaseous and unstable trifluoroacetaldehyde from its hemiacetal, and a successive asymmetric direct aldol reaction with various aldehydes in dichloromethane at 0\u2009\u00b0C, followed by reduction with sodium borohydride, gives 2\u2010substituted 4,4,4\u2010trifluorobutane\u20101,3\u2010diols in moderate to good yields (31\u201384\u2009%) with low diastereoselectivities and good to excellent enantioselectivities (64\u201397\u2009%\u2005<jats:italic>ee<\/jats:italic>).<\/jats:p>","DOI":"10.1002\/asia.201500607","type":"journal-article","created":{"date-parts":[[2015,7,21]],"date-time":"2015-07-21T05:16:06Z","timestamp":1437455766000},"page":"2701-2707","source":"Crossref","is-referenced-by-count":13,"title":["A Direct, Concise, and Enantioselective Synthesis of 2\u2010Substituted 4,4,4\u2010Trifluorobutane\u20101,3\u2010diols Based on the Organocatalytic In Situ Generation of Unstable Trifluoroacetaldehyde"],"prefix":"10.1002","volume":"10","author":[{"given":"Kazumasa","family":"Funabiki","sequence":"first","affiliation":[{"name":"Department of Chemistry and Biomolecular Science Gifu University  1-1 Yanagido Gifu Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Yudai","family":"Furuno","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Biomolecular Science Gifu University  1-1 Yanagido Gifu Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Yosuke","family":"Yano","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Biomolecular Science Gifu University  1-1 Yanagido Gifu Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Yuta","family":"Sakaida","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Biomolecular Science Gifu University  1-1 Yanagido Gifu Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Yasuhiro","family":"Kubota","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Biomolecular Science Gifu University  1-1 Yanagido Gifu Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Masaki","family":"Matsui","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Biomolecular Science Gifu University  1-1 Yanagido Gifu Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2015,8,17]]},"reference":[{"key":"e_1_2_6_1_1","unstructured":"For selected reviews see:"},{"key":"e_1_2_6_2_2","doi-asserted-by":"publisher","DOI":"10.1039\/c3np70076c"},{"key":"e_1_2_6_3_2","first-page":"557","author":"Bode S. 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Therefore before CF3CHO can be used it must be generated by using previous protocols which rely not only on the use of a large amount of concentrated H2SO4or P2O5 but also on a high reaction temperature. Furthermore the boiling point (\u221218\u2009\u00b0C) and high hygroscopicity of CF3CHO seem to cause handling problems at room temperature; see:"},{"key":"e_1_2_6_25_2","doi-asserted-by":"publisher","DOI":"10.5059\/yukigoseikyokaishi.57.898"},{"key":"e_1_2_6_26_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja01644a049"},{"key":"e_1_2_6_27_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja01164a013"},{"key":"e_1_2_6_28_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja01164a014"},{"key":"e_1_2_6_29_1","unstructured":"For recent examples on catalytic in situ generation of unstable fluorine-containing aldehydes and successive carbon\u2013carbon bond formation see:"},{"key":"e_1_2_6_30_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201500238"},{"key":"e_1_2_6_30_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201500238"},{"key":"e_1_2_6_31_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol502581b"},{"key":"e_1_2_6_32_1","doi-asserted-by":"publisher","DOI":"10.1002\/chir.10040"},{"key":"e_1_2_6_33_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo0497611"},{"key":"e_1_2_6_34_1","doi-asserted-by":"publisher","DOI":"10.1039\/c2cc32757k"},{"key":"e_1_2_6_35_1","unstructured":"For methyl ketones see:"},{"key":"e_1_2_6_36_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo026697j"},{"key":"e_1_2_6_37_2","doi-asserted-by":"publisher","DOI":"10.1039\/b408226e"},{"key":"e_1_2_6_37_3","doi-asserted-by":"publisher","DOI":"10.1021\/jo101733j"},{"key":"e_1_2_6_38_2","doi-asserted-by":"publisher","DOI":"10.1246\/cl.2010.410"},{"key":"e_1_2_6_39_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2006.05.165"},{"key":"e_1_2_6_39_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo200020z"},{"key":"e_1_2_6_40_1","doi-asserted-by":"publisher","DOI":"10.1055\/s-0030-1259543"},{"key":"e_1_2_6_40_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-0029-1260945"},{"key":"e_1_2_6_41_1","first-page":"556","volume-title":"Steric Effects in Organic Chemistry","author":"Taft R. 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