{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,1]],"date-time":"2026-10-01T17:58:23Z","timestamp":1790877503465,"version":"4.1.0"},"reference-count":189,"publisher":"Wiley","issue":"43","license":[{"start":{"date-parts":[[2009,9,22]],"date-time":"2009-09-22T00:00:00Z","timestamp":1253577600000},"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":[[2009,11,2]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>\n                    Full investigation of cyanation of aldehydes, ketones, aldimines and ketimines with trimethylsilyl cyanide (TMSCN) or ethyl cyanoformate (CNCOOEt) as the cyanide source has been accomplished by employing an in situ generated catalyst from cinchona alkaloid, tetraisopropyl titanate [Ti(O\n                    <jats:italic>i<\/jats:italic>\n                    Pr)\n                    <jats:sub>4<\/jats:sub>\n                    ] and an achiral modified biphenol. With TMSCN as the cyanide source, good to excellent results have been achieved for the Strecker reaction of\n                    <jats:italic>N<\/jats:italic>\n                    \u2010Ts (Ts=\n                    <jats:italic>p<\/jats:italic>\n                    \u2010toluenesulfonyl) aldimines and ketimines (up to &gt;99\u2009% yield and &gt;99\u2009%\n                    <jats:italic>ee<\/jats:italic>\n                    ) as well as for the cyanation of ketones (up to 99\u2009% yield and 98\u2009%\n                    <jats:italic>ee<\/jats:italic>\n                    ). By using CNCOOEt as the alternative cyanide source, cyanation of aldehyde was accomplished and various enantioenriched cyanohydrin carbonates were prepared in up to 99\u2009% yield and 96\u2009%\n                    <jats:italic>ee<\/jats:italic>\n                    . Noteworthy, CNCOOEt was successfully employed for the first time in the asymmetric Strecker reaction of aldimines and ketimines, affording various \u03b1\u2010amino nitriles with excellent yields and\n                    <jats:italic>ee<\/jats:italic>\n                    values (up to &gt;99\u2009% yield and &gt;99\u2009%\n                    <jats:italic>ee<\/jats:italic>\n                    ). The merits of current protocol involved facile availability of ligand components, operational simplicity and mild reaction conditions, which made it convenient to prepare synthetically important chiral cyanohydrins and \u03b1\u2010amino nitriles. Furthermore, control experiments and NMR analyses were performed to shed light on the catalyst structure. It is indicated that all the hydroxyl groups in cinchona alkaloid and biphenol complex with Ti\n                    <jats:sup>IV<\/jats:sup>\n                    , forming the catalyst with the structure of (biphenoxide)Ti(OR*)(O\n                    <jats:italic>i<\/jats:italic>\n                    Pr). The absolute configuration adopted by biphenol\n                    <jats:bold>4\u2009m<\/jats:bold>\n                    in the catalyst was identified as\n                    <jats:italic>S<\/jats:italic>\n                    configuration according to the evidence from control experiments and NMR analyses. Moreover, the roles of the protonic additive (\n                    <jats:italic>i<\/jats:italic>\n                    PrOH) and the tertiary amine in the cinchona alkaloid were studied in detail, and the real cyanide reagent in the catalytic cycle was found to be hydrogen cyanide (HCN). Finally, two plausible catalytic cycles were proposed to elucidate the reaction mechanisms.\n                  <\/jats:p>","DOI":"10.1002\/chem.200900936","type":"journal-article","created":{"date-parts":[[2009,9,22]],"date-time":"2009-09-22T10:33:06Z","timestamp":1253615586000},"page":"11642-11659","source":"Crossref","is-referenced-by-count":104,"title":["Asymmetric Cyanation of Aldehydes, Ketones, Aldimines, and Ketimines Catalyzed by a Versatile Catalyst Generated from Cinchona Alkaloid, Achiral Substituted 2,2\u2032\u2010Biphenol and Tetraisopropyl Titanate"],"prefix":"10.1002","volume":"15","author":[{"given":"Jun","family":"Wang","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Wentao","family":"Wang","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Wei","family":"Li","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xiaolei","family":"Hu","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ke","family":"Shen","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Cheng","family":"Tan","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xiaohua","family":"Liu","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xiaoming","family":"Feng","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2009,10,23]]},"reference":[{"key":"e_1_2_6_1_2","first-page":"246","volume":"4","author":"Winkler F. 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Ed."},{"key":"e_1_2_6_126_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol0702674"},{"key":"e_1_2_6_127_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo701307f"},{"key":"e_1_2_6_128_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2006.12.122"},{"key":"e_1_2_6_129_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200703179"},{"key":"e_1_2_6_129_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200703179"},{"key":"e_1_2_6_130_2","doi-asserted-by":"publisher","DOI":"10.1002\/asia.200700327"},{"key":"e_1_2_6_131_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.200700763"},{"key":"e_1_2_6_132_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200800319"},{"key":"e_1_2_6_133_2","unstructured":"For the asymmetric Strecker reaction of ketimines see:"},{"key":"e_1_2_6_134_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol005636"},{"key":"e_1_2_6_135_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(99)02215-7"},{"key":"e_1_2_6_136_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja027246j"},{"key":"e_1_2_6_137_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja034980"},{"key":"e_1_2_6_138_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2004.02.077"},{"key":"e_1_2_6_139_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2004.02.082"},{"key":"e_1_2_6_140_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja060841r"},{"key":"e_1_2_6_141_2","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.200600238"},{"key":"e_1_2_6_142_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo062006y"},{"key":"e_1_2_6_143_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200703188"},{"key":"e_1_2_6_143_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200703188"},{"key":"e_1_2_6_144_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200800454"},{"key":"e_1_2_6_145_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200900210"},{"key":"e_1_2_6_146_2","unstructured":"For reviews on the asymmetric activation of racemic ligands see:"},{"key":"e_1_2_6_147_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr0000630"},{"key":"e_1_2_6_148_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr0200318"},{"key":"e_1_2_6_149_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr000260z"},{"key":"e_1_2_6_150_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200305707"},{"key":"e_1_2_6_151_2","unstructured":"Part of the data in this article was communicated previously; see ref.\u2005[11j]."},{"key":"e_1_2_6_152_2","unstructured":"Isopropanol was added in one portion. Slow addition ofiPrOH was unnecessary to ensure high enantioselectivity. For some discussions of the role of protic additives see: ref. 10f h. For selected examples using protonic additive to achieve good results see: ref.\u2005[8f \u2009r s \u200910f\u2013h \u2009n \u200911f\u2013k]."},{"key":"e_1_2_6_153_2","unstructured":"Cyanide agents including tri\u2010n\u2010butyltin cyanide ((nBu)3SnCN) acetone cyanohydrin and acetyl cyanide (CH3COCN) were examined. Compared with TMSCN generally much lower reactivities were observed under otherwise identical reaction conditions."},{"key":"e_1_2_6_154_2","unstructured":"For reviews see:"},{"key":"e_1_2_6_155_2","volume-title":"Comprehensive Asymmetric Catalysis","year":"1999"},{"key":"e_1_2_6_156_2","first-page":"454","volume":"35","author":"Schmidt F.","year":"2006","journal-title":"Chem. Soc. Rev."},{"key":"e_1_2_6_157_2","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.0409043102"},{"key":"e_1_2_6_158_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol060927p"},{"key":"e_1_2_6_159_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol0627909"},{"key":"e_1_2_6_160_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo7016718"},{"key":"e_1_2_6_161_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol801590j"},{"key":"e_1_2_6_162_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol060755w"},{"key":"e_1_2_6_163_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200504309"},{"key":"e_1_2_6_163_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200504309"},{"key":"e_1_2_6_164_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0710914"},{"key":"e_1_2_6_165_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol801574m"},{"key":"e_1_2_6_166_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja071523a"},{"key":"e_1_2_6_167_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(02)01200-5"},{"key":"e_1_2_6_168_2","unstructured":"Although CNCOOEt was successfully used in the cyanation of aliphatic ketones the reaction of CNCOOEt with aromatic ketones was not mentioned in Deng\u2019s report (see: ref.\u2005[8e]). In addition Belokon\u2032 and North\u2019s attempt to employ CNCOOEt as the cyanide source in the cyanation of ketones also failed (see ref.\u2005[6d e])."},{"key":"e_1_2_6_169_2","unstructured":"When1\u2009a\/Ti\/4\u2009m1:1:1 or1\u2009b\/Ti\/4\u2009m1:1:1 was used instead of1\u2009b\/Ti\/4\u2009m2:2:1 although the enantioselectivity was excellent (99\u2009%\u2005ee) longer reaction time (78\u2005h) was required to complete the reaction. On the other hand lowering the catalyst loading from 10 to 5\u2005mol\u2009% led to a dramatic decrease in reaction rate and 95\u2009% yield and 99\u2009%\u2005eewere obtained after 5\u2005d."},{"key":"e_1_2_6_170_2","unstructured":"The spectrum was obtained in positive\u2010ion mode by stepwise diluting the toluene or CDCl3solution of1\u2009b\/Ti\/4\u2009m1:1:1 with acetonitrile."},{"key":"e_1_2_6_171_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00368a030"}],"container-title":["Chemistry \u2013 A European Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fchem.200900936","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.200900936","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T19:28:25Z","timestamp":1760297305000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/chem.200900936"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2009,10,23]]},"references-count":189,"journal-issue":{"issue":"43","published-print":{"date-parts":[[2009,11,2]]}},"alternative-id":["10.1002\/chem.200900936"],"URL":"https:\/\/doi.org\/10.1002\/chem.200900936","archive":["Portico"],"relation":{},"ISSN":["0947-6539","1521-3765"],"issn-type":[{"value":"0947-6539","type":"print"},{"value":"1521-3765","type":"electronic"}],"subject":[],"published":{"date-parts":[[2009,10,23]]}}}